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Journal articles on the topic 'Piperidina'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Šilhánková, Alexandra, Karel Šindelář, Karel Dobrovský, Ivan Krejčí, Jarmila Hodková, and Zdeněk Polívka. "Synthesis of New L-Proline Amides with Anticonvulsive Effect." Collection of Czechoslovak Chemical Communications 61, no. 7 (1996): 1085–92. http://dx.doi.org/10.1135/cccc19961085.

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Series of heterocyclic L-proline amides were prepared from BOC-L-proline and heterocyclic amines (mostly substituted piperazines and morpholines) via active ester with hydroxysuccinimide. 4-(4-Fluorobenzoyl)piperidine afforded L-proline 4-(4-(4-(4-fluorobenzoyl)piperidin-1-yl)benzoyl)piperidine (7b) simultaneously with expected L-proline 4-(4-fluorobenzoyl)piperidide (7a). D-Proline N-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)amide (2) was prepared starting from D-proline. The amides were tested by methods of biochemical and behavioural pharmacology.

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2

González Garcia, Filiberto, and Bluma G. Soares. "Separação de fases induzida por meio de reação química no sistema éter diglicidílico do bisfenol A e piperidina com poli(metacrilato de metila)." Polímeros 13, no. 4 (2003): 235–41. http://dx.doi.org/10.1590/s0104-14282003000400008.

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O comportamento da separação de fases e da gelificação do sistema epoxídico, constituído pelo éter diglicidílico do bisfenol A (DGEBA) e a piperidina, modificado com poli(metacrilato de metila) (PMMA), foi estudado na faixa de temperatura de 60 °C - 120 °C. A concentração de PMMA e a temperatura de cura causam mudanças significativas na morfologia gerada. A massa molecular de PMMA provoca ligeiras mudanças para a observação da separação de fases e não afeta a velocidade da reação. O sistema modificado com PMMA mostra o efeito de retardação cinético e a velocidade de separação de fases é maior

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3

Jílek, Jiří, Miroslav Rajšner, Vladimír Valenta, et al. "Synthesis of piperidine derivatives as potential analgetic agents." Collection of Czechoslovak Chemical Communications 55, no. 7 (1990): 1828–53. http://dx.doi.org/10.1135/cccc19901828.

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Reaction of N-(1-(2-phenylethyl)-4-piperidinyl)propionanilide (I) with phosphorus pentasulfide gave the thioamide VI. Acylation of N-(1-(2-phenylethyl)-4-piperidinyl)aniline with 2-(methoxy)acetic and 2-(methylthio)acetic anhydrides afforded the amides II and III. Treatment of 4-anilino-1-benzylpiperidine-4-methanol with thionyl chloride gave the spirocyclic sulfurous acid ester amide XIV. Reduction of the hydrochloride of ethyl 3-(1-ethoxycarbonyl-4-phenylimino-3-piperidinyl)propionate (XXII) with sodium cyanoborohydride gave the perhydro-1,6-naphthyridine derivative XIX, a model compound in

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4

Romero, Nancy, Sylvain Bernès, Luis F. Roa, Joel L. Terán, and Dino Gnecco. "Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hydroxy-1-phenylethyl]piperidin-4-one and 8-[(1S)-1-phenylethyl]-1,4-dioxa-8-azaspiro[4.5]decane-7-thione." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (2015): 1207–11. http://dx.doi.org/10.1107/s2056989015017119.

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The crystal structures of the two title piperidine derivatives show different conformations for the six-membered heterocycle. TheN-substituted 4-piperidinone 1-[(1R)-2-hydroxy-1-phenylethyl]piperidin-4-one, C13H17NO2, (I), has a chair conformation, while the piperidine substituted in position 2 with a thiocarbonyl group, 8-[(1S)-1-phenylethyl]-1,4-dioxa-8-azaspiro[4.5]decane-7-thione, C15H19NO2S, (II), features a half-chair conformation. Comparison of the two structures, and data retrieved from the literature, suggests that the conformational flexibility is mainly related to the hybridization

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5

K, Manjusha R., Shaheen Begum, Arifa Begum, and Bharathi K. "ANTIOXIDANT POTENTIAL OF PIPERIDINE CONTAINING COMPOUNDS-A SHORT REVIEW." Asian Journal of Pharmaceutical and Clinical Research 11, no. 8 (2018): 66. http://dx.doi.org/10.22159/ajpcr.2018.v11i8.26536.

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Piperidine is a saturated heterocyclic ring, considered as a privileged scaffold in view of its role in wide range of biological activities. Piperidine is good candidate molecule for obtaining potent antioxidant agents. The planar nature of this heterocyclic nucleus allows the introduction of substituent groups at different positions on the ring. In the present review, the antioxidant profile of piperidine containing compounds has been focused. The compounds were classified into naturally occurring piperidines, unsaturated piperidines, N-substituted piperidines, piperamides, piperanols, piperi

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6

Kalinowska-Tłuścik, Justyna, Agata Piaskowska, and Marcin Kołaczkowski. "Multifunctional arylsulfonamide derivatives with 5-HT6/5-HT7 receptor antagonistic activity: a structural study." Acta Crystallographica Section C Structural Chemistry 74, no. 11 (2018): 1477–86. http://dx.doi.org/10.1107/s2053229618013748.

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Nowadays, a search for antagonists co-acting on serotonin receptor subtypes 6 and 7 (5-HT6R and 5-HT7R, respectively) is of great interest due to the increasing number of patients suffering from dementia and related behavioural and psychological symptoms. The X-ray crystal structures of four promising multifunctional ligands in the hydrochloride forms were determined, namely 4-(6-fluoro-1,2-benzoxazol-3-yl)-1-[3-(3-methylbenzenesulfonamido)propyl]piperidin-1-ium chloride, C22H27FN3O3S+·Cl−, (I), 4-(6-fluoro-1,2-benzoxazol-3-yl)-1-[4-(5-fluoro-3-methylbenzo[b]thiophene-2-sulfonamido)butyl]piper

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7

Viswanathan, Vijayan, Ayyavu Thirunarayanan, Perumal Rajakumar, and Devadasan Velmurugan. "An amide cyclophane." Acta Crystallographica Section E Structure Reports Online 70, no. 8 (2014): o865. http://dx.doi.org/10.1107/s1600536814015621.

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The title compound, 8,18-dithia-2,6-diaza-13(1,4)-piperidina-1(1,2),4(1,3),7(1,2)-tribenzenaoctadecaphane-10,15-diyne-3,6-dione, C32H30N4O2S2, is composed of a relatively planar bis(2-mercaptophenyl)isophthalamide unit linked to a bridging 1,4-di(but-2-yn-1-yl)piperazine unit, forming a macrocycle. The isophthalamide ring is inclined to the outer mercaptophenyl rings by 8.18 (11) and 5.59 (10)°, while these two rings are inclined to one another by 9.10 (12)°. The piperazine ring adopts a chair conformation. There are two intramolecular N—H...S hydrogen bonds generatingS(5) ring motifs. In the

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8

Gelbrich, Thomas, Denise Rossi, and Ulrich J. Griesser. "Two polymorphs and the diethylammonium salt of the barbiturate eldoral." Acta Crystallographica Section C Crystal Structure Communications 68, no. 2 (2012): o65—o70. http://dx.doi.org/10.1107/s0108270111055120.

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Polymorph (Ia) of eldoral [5-ethyl-5-(piperidin-1-yl)barbituric acid or 5-ethyl-5-(piperidin-1-yl)-1,3-diazinane-2,4,6-trione], C11H17N3O3, displays a hydrogen-bonded layer structure parallel to (100). The piperidine N atom and the barbiturate carbonyl group in the 2-position are utilized in N—H...N and N—H...O=C hydrogen bonds, respectively. The structure of polymorph (Ib) contains pseudosymmetry elements. The two independent molecules of (Ib) are connectedviaN—H...O=C(4/6-position) and N—H...N(piperidine) hydrogen bonds to give a chain structure in the [100] direction. The hydrogen-bonded la

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9

Rádl, Stanislav, Wieland Hafner, Petr Hezký, Ivan Krejčí, Jan Proška, and Jan Taimr. "Molecular Modification of Anpirtoline, a Non-Opioid Centrally Acting Analgesic." Collection of Czechoslovak Chemical Communications 64, no. 2 (1999): 363–76. http://dx.doi.org/10.1135/cccc19990363.

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Molecular modification of anpirtoline (2a) is described. Several methods of preparation of 4-[(3-chlorophenyl)sulfanyl]-1-methylpiperidine (3a) and its demethylation led to the deazaanpirtoline (3c). Nucleophilic substitution of piperidine-4-thiole with 2-chloro-4-nitropyridine, 2,4-dichloro-6-methylpyridine, and 3,6-dichloropyridazine led to 2-chloro-4-(piperidin-4-ylsulfanyl)pyridine (6), 4-chloro-6-methyl-2-(piperidin-4-ylsulfanyl)pyridine (7), and 3-chloro-6-(piperidin-4-ylsulfanyl)pyridazine (8), respectively. 2-Chloro-6-(pyridin-4-ylsulfanyl)pyridine (10) and 4-[(2-chloropyridin-6-yl)sul

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10

Guzmán-Rodríguez, Sergio, Jesús Chávez-Reyes, Priscila Vázquez-León, et al. "1-Boc-Piperidine-4-Carboxaldehyde Prevents Binge-Eating Behaviour and Anxiety in Rats." Pharmacology 106, no. 5-6 (2021): 305–15. http://dx.doi.org/10.1159/000513376.

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<b><i>Background:</i></b> Piperidines are biogenic amines studied mainly in toxicology because they were initially found as alkaloids from peppers and insect venoms. Piperidines are also produced in the human body, and their actions seem to be related to wakefulness/sleep and other cognitive phenomena. Piperidines have been minimally characterized for therapeutic applications. In this context, 1-Boc-piperidine-4-carboxaldehyde (1-Boc-piperidine) is a piperidine-derivative molecule with no mechanism of action reported, although its uses include the synthesis of GPR119 se

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11

Ariffin, Eda Yuhana, Yook Heng Lee, Ling Ling Tan, and Nurul Huda Abd Karim. "Sintesis dan Pencirian Kompleks Nikel(II) Salfen dengan Rantai Sisi Piperidina dan Kajian Interaksi dengan DNA Denggi." Sains Malaysiana 47, no. 6 (2018): 1139–46. http://dx.doi.org/10.17576/jsm-2018-4706-09.

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12

Chakkaravarthy, Jayaraman, Inbasekaran Muthuvel, and Ganesamoorthy Thirunarayanan. "Spectral investigations of some piperidin-4-one molecular addition compounds." Ovidius University Annals of Chemistry 31, no. 1 (2020): 18–26. http://dx.doi.org/10.2478/auoc-2020-0005.

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AbstractIn the present study, some 2- and 3-substituted piperidin-4-ones (A1-A3) were chosen as proton acceptor and maleic anhydride was chosen as proton donor. Piperidin-4-ones (A1, A2 ---amp--- A3) were mixed with maleic anhydride in ether medium and the corresponding molecular adduct products (B1, B2 ---amp--- B3) thus obtained were collected and purified. The 1H and 13C NMR spectra were recorded for piperidine-4-one and their addition compounds. The 1H and 13C NMR chemical shifts of products (B1, B2 ---amp--- B3) are analyzed and compared with those of the corresponding piperidine-4-ones (

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13

Tilve, Santosh, Sandesh Bugde, and Prajesh S.Volvoikar. "Protecting-Group-Directed Regio- and Stereoselective Oxymercuration–Demercuration: Synthesis of Piperidine Alkaloids Containing 1,2- and 1,3-Amino Alcohol Units." Synthesis 50, no. 05 (2017): 1113–22. http://dx.doi.org/10.1055/s-0036-1589523.

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An efficient synthesis of naturally occurring 1,2- and 1,3-amino alcohol unit containing 2-substituted piperidine alkaloids and their analogues has been developed from l-pipecolinic acid. The protocol describes the regio- and stereoselective oxymercuration–demercuration of 2-alkenyl piperidines based on protecting groups to give piperidine alkaloids as a key step.

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14

Matulevičiūtė, Gita, Eglė Arbačiauskienė, Neringa Kleizienė, et al. "Synthesis and Characterization of Novel Methyl (3)5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates." Molecules 26, no. 13 (2021): 3808. http://dx.doi.org/10.3390/molecules26133808.

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Series of methyl 3- and 5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates were developed and regioselectively synthesized as novel heterocyclic amino acids in their N-Boc protected ester form for achiral and chiral building blocks. In the first stage of the synthesis, piperidine-4-carboxylic and (R)- and (S)-piperidine-3-carboxylic acids were converted to the corresponding β-keto esters, which were then treated with N,N-dimethylformamide dimethyl acetal. The subsequent reaction of β-enamine diketones with various N-mono-substituted hydrazines afforded the target 5-(N-Boc-piperidinyl)-1H-pyrazol

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15

González Garcia, Filiberto, Maria E. Leyva, and Alvaro A. A. de Queiroz. "Influência da estrutura química do co-monômero nas propriedades termomecânicas e durabilidade de uniões adesivas submetidas à ação da água." Polímeros 21, no. 4 (2011): 253–58. http://dx.doi.org/10.1590/s0104-14282011005000057.

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A caracterização termomecânica, assim como a durabilidade de juntas adesivas usando diferentes polímeros epoxídicos no estado vítreo foram analisadas. Os polímeros foram baseados no prepolímero do éter diglicidílico do bisfenol A (DGEBA) curado com diferentes aminas alifáticas. Análises termomecânicas no modo de torção foram realizadas para monitorar o fator de perda (tan δ), o módulo de armazenamento (G'), e o módulo de perda (G") em função da temperatura. Os ensaios de adesão foram realizados em uniões de simples sobreposição usando substrato de aço quando submetidas à ação da água a tempera

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16

Pelletier, Guillaume, Léa Constantineau-Forget, and André B. Charette. "Directed functionalization of 1,2-dihydropyridines: stereoselective synthesis of 2,6-disubstituted piperidines." Chem. Commun. 50, no. 52 (2014): 6883–85. http://dx.doi.org/10.1039/c4cc02220c.

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A practical and highly stereoselective approach to access 2,6-disubstituted piperidines using an amidine auxiliary is reported. These were reduced to the saturated piperidine rings with high diastereoselectivity.

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17

Penjisevic, Jelena, Vladimir Sukalovic, Deana Andric, et al. "Synthesis, biological evaluation and docking analysis of substituted piperidines and (2-methoxyphenyl)piperazines." Journal of the Serbian Chemical Society 81, no. 4 (2016): 347–56. http://dx.doi.org/10.2298/jsc151021097p.

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A series of sixteen novel substituted piperidines and (2-methoxyphenyl)piperazines were synthesized, starting from the key intermediates 1-(2-methoxyphenyl)-4-(piperidin-4-yl)piperazine and 1-(2-methoxyphenyl)-4-(piperidin-4-ylmethyl)piperazine. Biological evaluation of the synthesized compounds was pointed out for seven compounds, of which 1-(2-methoxyphenyl)-4-{[1-(2-nitrobenzyl)piperidin-4-yl]methyl}piperazine had the highest affinity for the dopamine D2 receptor. For all seven selected compounds docking analysis was performed in order to establish their structure-to-activity relationship.

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18

Eckhardt, Tamira, Richard Goddard, Ines Rudolph, et al. "[2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis." Acta Crystallographica Section E Crystallographic Communications 76, no. 9 (2020): 1442–46. http://dx.doi.org/10.1107/s2056989020010658.

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1,3-Benzothiazin-4-ones (BTZs) are a promising new class of anti-tuberculosis drug candidates, some of which have reached clinical trials. The title compound, the benzamide derivative [2-chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone, C13H12ClF3N2O3, occurs as a side product as a result of competitive reaction pathways in the nucleophilic attack during the synthesis of the BTZ 8-nitro-2-(piperidin-1-yl)-6-(trifluoromethyl)-1,3-benzothiazin-4-one, following the original synthetic route, whereby the corresponding benzoyl isothiocyanate is reacted with piperidine as secondary

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19

Elavarasan, Thangasamy, Durairaj Peter Bhakiaraj, and Mannathusamy Gopalakrishnan. "Synthesis, Spectral Analysis, In Vitro Microbiological Evaluation, and Molecular Docking Studies of Some Novel 1-(1-Aryl-1H-tetrazol-5-yl)-2-(piperidin-1-yl)ethanone Derivatives." ISRN Organic Chemistry 2014 (May 6, 2014): 1–9. http://dx.doi.org/10.1155/2014/120173.

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A new series of novel heterocyclic compounds containing both tetrazoles and piperidine nuclei together, namely, 1-(1-aryl-1H-tetrazol-5-yl)-2-(piperidin-1-yl)ethanone (22–28), were synthesized by the treatment of the respective 2-chloro-1-(1-aryl-1H-tetrazol-5-yl)ethanone (15–21) with piperidine in acetonitrile for 6 h. A series of novel tetrazole substituted piperidine derivatives were synthesized and evaluated for their antimicrobial activity using serial dilution method. The structures of the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, mass spectral data, and elemental

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20

Du, Rui, Liangliang Han, Zhongqiang Zhou, and Victor Borovkov. "Efficient Synthesis of Novel Quinolinone Derivatives via Catalyst-free Multicomponent Reaction." Letters in Organic Chemistry 17, no. 5 (2020): 403–7. http://dx.doi.org/10.2174/1570178616666190828092728.

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The synthesis of 3-(aryl(piperidin-1-yl)methyl)-4-hydroxyquinolin-2(1H)-one derivatives via catalyst-free multicomponent reaction is described. The reaction of 4-hydroxyquinolin-2(1H)-one, piperidine, and 4-chlorobenzaldehyde was carried out in different solvents and under solvent-free conditions at room temperature. The best solvent in terms of the yield and reaction time was found to be dichloromethane. Most substituted benzaldehydes reacted with 4-hydroxyquinolin-2(1H)-one and piperidine to afford corresponding products in good-to-excellent yields. Aldehydes with electronwithdrawing groups

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21

López-Rodríguez, Alberto, Gema Domínguez, and Javier Pérez-Castells. "Synthesis of Novel Iminosugar Derivatives Based on a 2-Azabicyclo[4.1.0]heptane Skeleton." Synthesis 49, no. 20 (2017): 4606–12. http://dx.doi.org/10.1055/s-0036-1589109.

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Iminosugars are good starting points for the development of different kinds of drugs. Many are polyhydroxylated piperidines that behave as biomimetics of their corresponding pyranoses analogues. In the interaction with carbohydrate processing enzymes, selectivity is a crucial issue and the benefits of introducing a cyclopropane bridge in a piperidine structure is demonstrated. The synthesis of novel bicyclic piperidine-based iminosugars using a sulfur ylide cyclopropanation as the key synthetic step is described.

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22

Jothivel, S., Jibon Kotoky, and S. Kabilan. "Crystal structure of 1-(2-chloroacetyl)-3,3-dimethyl-2,6-di-p-tolylpiperidin-4-one." Acta Crystallographica Section E Crystallographic Communications 71, no. 3 (2015): o173—o174. http://dx.doi.org/10.1107/s2056989015002613.

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In the title compound, C23H26ClNO2, the piperidin-4-one ring adopts a distorted boat conformation. The twop-tolyl rings are nearly normal to each other, making a dihedral angle of 83.33 (10)°. They are inclined to the mean plane of the piperidine ring by 73.2 (1) and 87.22 (9)°. In the crystal, there are no significant intermolecular interactions present.

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23

Wang, Zhe-Qin, and Yi Ma. "1-[(3-Nitrophenyl)(piperidin-1-yl)methyl]piperidine." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1941. http://dx.doi.org/10.1107/s1600536812023525.

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24

Klegraf, Ellen, and Horst Kunz. "Stereoselective Synthesis of 3-Substituted and 3,4-Disubstituted Piperidine und Piperidin-2-one Derivatives." Zeitschrift für Naturforschung B 67, no. 4 (2012): 389–405. http://dx.doi.org/10.1515/znb-2012-0413.

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The stereoselective synthesis of 3-substituted and 3,4-disubstituted piperidine and piperidin-2-one derivatives was achieved starting from 2-pyridone. After N-galactosylation and subsequent O-silylation, nucleophilic addition of organometallic reagents proceeded with high regio- and stereoselectivity at 4-position. Substituents at position 3 were stereoselectively introduced by reaction of electrophiles with amide enolates of the N-galactosyl-2-piperidones.

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25

Liu, Hui Xian, Dao Wei Huang, and Yue Zhang. "Synthesis of 3-Methyl-1-[2-(1-Piperidiny) Phenyl]-butyl Amine." Advanced Materials Research 396-398 (November 2011): 1527–30. http://dx.doi.org/10.4028/www.scientific.net/amr.396-398.1527.

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3-Methyl-1-[2-(1-piperidiny) phenyl]-butyl amine (1) is an important intermediate for synthesis of Repaglinide, a well-known oral medicine for diabetes. It has been reported that 1 could be obtained from o-flurobenzaldehyde undergoing Grignard reaction, oxidition, piperidine substitution, oximation and reduction. In the process of reduction, the oximate 3-methyl-1-[2-(1-piperidiny) phenyl]-butyl oxime (6) was reduced by NiCl2-NaBH4 with many impurities, difficult workup, low yield and a lot of environmental problems. Herein the environmental friendly catalytic hydrogenation with simple work-up

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26

Méndez, Leonor, and Vladimir Kouznetsov. "Intramolecular N to N acyl migration in conformationally mobile 1′-acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinoline] systems promoted by debenzylation conditions (HCOONH4/Pd/C)." Open Chemistry 9, no. 5 (2011): 877–85. http://dx.doi.org/10.2478/s11532-011-0082-y.

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AbstractWe report an efficient and useful synthesis of new attractive spiropiperdine scaffolds 4 based on an intramolecular acyl transfer process in 1′-acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinolines] 3 using simple and mild debenzylation reaction conditions (HCOONH4/Pd/C). The compounds 3 were prepared by acylating 1-benzyl-4′-methyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinolines] 2 that are easily available from 1-benzyl-4-piperidone 1. The intramolecular character of this process was proven primarily through a crossover experiment technique. Through an examination of al

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27

Šindelář, Karel, Jan Metyš, and Miroslav Protiva. "Potential antidiarrheal agents: 1-(11-Cyano-6,11-dihydrodibenzo[b,e]thiepin-11-yl-alkyl)- and 1-(10-cyano-10,11-dihydrodibenzo[b,f]thiepin-10-yl-alkyl)-4-substituted piperidines." Collection of Czechoslovak Chemical Communications 50, no. 5 (1985): 1089–96. http://dx.doi.org/10.1135/cccc19851089.

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Substitution reactions of 11-(2-bromoethyl)- and 11-(3-bromopropyl)-6,11-dihydrodibenzo[b,e]thiepin-11-carbonitrile and further of 10-(2-bromoethyl)- and 10-(3-bromopropyl)-10,11-dihydrodibenzo[b,f]thiepin-10-carbonitrile with ethyl 4-phenylpiperidine-4-carboxylate, 4-phenylpiperidin-4-ol, 4-(2-tolyl)piperidin-4-ol, 4-(4-fluorophenyl)piperidin-4-ol, 4-(2-oxobenzimidazolin-1-yl)-piperidine and 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one afforded the tricyclic piperidinoalkyl nitriles IV-XIII which are cyclic analogues of the antidiarrheal agents diphenoxylate (I) and loperamide (III). Out of the

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28

Šilhánková, Alexandra, Michal Hoskovec, Radek Liboska, and Miloslav Ferles. "Mannich and Grignard reaction of some N-(2-propynyl)azaheterocycles." Collection of Czechoslovak Chemical Communications 54, no. 4 (1989): 1067–81. http://dx.doi.org/10.1135/cccc19891067.

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1,4-Disubstituted butynes IV-VII were prepared by Mannich reaction of N-(2-propynyl) derivatives of 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline, piperidine and azacycloheptane with polyoxymethylene and another heterocyclic amines. Reaction of 3-(1-piperidinyl)-1-propynylmagnesium bromide or 3-(1-azacycloheptyl)-1-propynylmagnesium bromide afforded alcohols X-XIII.

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29

Li, Ning, Xianyong Bai, Lianshuang Zhang, and Yun Hou. "Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives." Acta Crystallographica Section C Structural Chemistry 74, no. 10 (2018): 1171–79. http://dx.doi.org/10.1107/s2053229618013232.

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3,5-Bis(arylidene)-4-piperidone (BAP) derivatives display good antitumour and anti-inflammatory activities because of their double α,β-unsaturated ketone structural characteristics. If N-benzenesulfonyl substituents are introduced into BAPs, the configuration of the BAPs would change significantly and their anti-inflammatory activities should improve. Four N-benzenesulfonyl BAPs, namely (3E,5E)-1-(4-methylbenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate, C28H21F6NO3S·CH2Cl2, (4), (3E,5E)-1-(4-fluorobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)b

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30

S, Harishkumar, Satyanarayan Nd, and Santhosha Sm. "ANTIPROLIFERATIVE AND IN SILICO ADMET STUDY OF NEW 4-(PIPERIDIN-1-YLMETHYL)-2- (THIOPHEN-2-YL) QUINOLINE ANALOGUES." Asian Journal of Pharmaceutical and Clinical Research 11, no. 4 (2018): 306. http://dx.doi.org/10.22159/ajpcr.2018.v11i4.24147.

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Objective: Synthesis and antiproliferative study of novel 4-(piperidin-1-ylmethyl)-2-(thiophen-2-yl) quinoline 7(a-j) derivatives.Methods: 4-(piperidin-1-ylmethyl)-2-(thiophen-2-yl) quinolines were synthesized by the addition of 4-(chloromethyl)-2-(thiophen-2-yl) quinoline (0.01 mol), piperidine (0.01 mol) in DMF (10 v) and K2CO3 (0.02 mol). The anticancer activity of the title compounds performed against T-47D, HeLa, HepG2, and MCF-7 human cancer cell lines growth was investigated by MTT assay.Results: The compounds 7b and 7g exhibited 90% of the growth inhibitory effect on T-47D, HeLa, and M

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31

Möhrle, H., and M. Jeandrée. "Chinazolinderivate durch Cyclodehydrierung von N-(2-substituierten Aryl)-Piperidinen / Quinazoline Derivatives by Cyclodehydrogenation of N-(2-Substituted Aryl)-Piperidines." Zeitschrift für Naturforschung B 54, no. 12 (1999): 1577–88. http://dx.doi.org/10.1515/znb-1999-1217.

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Dehydrogenation of the N-[2-(aminocarbonyl)phenyl]piperidines 1 -5 using Hg(II)-EDTA, generated the quinazolinones 6 -9 . Increasing size of the 4-substituent in the piperidine decreased the oxidation rate and the product yield.N-[2-(Hydroxyiminomethyl)phenyl]piperidines 18-22 showed a different behaviour. While 18 with H g(II)-EDTA in water produced the oxime lactam 24 in quantitative yield, the 4- substituted piperidines 19-21 caused not only a lower reaction rate but also an altered product pattern. The double dehydrogenation to lactams was reduced and the cyclic nitrones, formed by two ele

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32

Gao, Hong, Jing Sun, and Chao-Guo Yan. "Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate." Beilstein Journal of Organic Chemistry 9 (December 27, 2013): 2934–39. http://dx.doi.org/10.3762/bjoc.9.330.

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The four-component reaction of 2-aminobenzothiazole, aromatic aldehydes, acetylenedicarboxylate and piperidine or pyrrolidine in ethanol afforded the functionalized 2-pyrrolidinones containing both benzothiazolyl and piperidinyl (or pyrrolidinyl) units in good yields. On the other hand, the similar four-component reactions resulted in the functionalized morpholinium or piperidinium 2-pyrrolidinon-3-olates in the presence of p-toluenesulfonic acid.

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33

Sartillo-Piscil, Fernando, Julio Romero-Ibañez, Silvano Cruz-Gregorio, and Leticia Quintero. "Concise and Environmentally Friendly Asymmetric Total Synthesis of the Putative Structure of a Biologically Active 3-Hydroxy-2-piperidone Alkaloid." Synthesis 50, no. 15 (2018): 2878–86. http://dx.doi.org/10.1055/s-0037-1610089.

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An asymmetric total synthesis of stereoisomers of a putative structure of 3-hydroxy-2-piperidone alkaloid derivative is described. This route is not only concise and efficient but also is achieved under an environmentally friendly approach. To this end, a direct and double C–H oxidation reaction of simple benzylated piperidine and Baker’s yeast reduction of a carbonyl group allowed the rapid access to the optically enriched (S)-1-benzyl-3-hydroxy-2-piperidone in only three steps. The NMR data agreed with those obtained in the first total synthesis (and in discrepancy with the natural product),

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Talbot, Eric. "Synthesis of Polyfunctionalised 2-Piperidinones Catalysed by Fe(acac)3." Synlett 30, no. 07 (2019): 821–26. http://dx.doi.org/10.1055/s-0037-1610700.

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Herein is reported the synthesis of polyfunctionalised piperidines and 2-piperidinones, through hydrogen atom transfer (HAT) chemistry catalysed by Fe(acac)3. The nature and substitution around the Michael acceptor, as well as the allylic amine, allowed access to all positions of the piperidine ring. The chemistry tolerates a range of different functionalities, allowing the investigation of new and diverse scaffolds.

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Ivanović, Milovan, Ivana Jevtić, Ljiljana Došen-Mićović, Evica Ivanović, and Nina Todorović. "Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3-N-Carbomethoxyfentanyl." Synthesis 49, no. 14 (2017): 3126–36. http://dx.doi.org/10.1055/s-0036-1588985.

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The synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (±)-cis and (±)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The

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Wang, Guo-Ming, Xiao-Meng Zhao, Xiao Zhang та Zhen-Zhen Bao. "The inorganic–organic hybrid zinc phosphite poly[(μ3-hydrogen phosphito-κ3O:O′:O′′)(piperidin-1-ium-4-carboxylate-κO)zinc(II)]". Acta Crystallographica Section C Structural Chemistry 70, № 3 (2014): 289–91. http://dx.doi.org/10.1107/s2053229614003118.

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A new inorganic–organic hybrid zinc phosphite, [Zn(HPO3)(C6H11NO2)]n, has been synthesized hydrothermally. Protonated piperidin-1-ium-4-carboxylate (PDCA) was generatedin situby hydrolysis of the piperidine-4-carboxamide precursor. The P atom possesses a typical PO3H pseudo-pyramidal geometry. The crystal structure features an unusual (3,4)-connected two-dimensional inorganic zinc–phosphite layer, with organic PDCA ligands appended to the sheets and protruding into the interlayer region. Helical chains of opposite chirality are involved in the construction of a puckered sheet structure.

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Möhrle, H., and J. Mehrens. "Reaktivität nitrophenylsubstituierter cyclischer Amine bei Dehydrierungen / The Reactivity of Nitrophenyl Substituted Cyclic Amines with Dehydrogenations." Zeitschrift für Naturforschung B 53, no. 1 (1998): 37–48. http://dx.doi.org/10.1515/znb-1998-0109.

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Piperidine and perhydroazepine bearing a 1 -(4-nitrophenyl) substituent were inert to mercury-edta, while the a-pipecoline derivative gave an aminoketone with cleavage of the heterocycle. However the corresponding (2-nitrophenyl) compounds reacted to give respectively a piperidin-2-one, an aminopentanal and an aminohexanone.By an additional substituent in 2′-position the p-nitro compounds underwent dehydrogenation too. With a methyl group resulted a pattern analogous to o-nitro products. A neighbouring hydroxymethyl function enhanced the reaction with formation of benzoxazines and if possible

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Revathi, B. K., D. Reuben Jonathan, K. Kalai Sevi, K. Dhanalakshmi, and G. Usha. "Crystal structure of the adduct (4-chlorophenyl)(4-hydroxypiperidin-1-yl)methanone–(4-chlorophenyl)(piperidin-1-yl)methanone (0.75/0.25)." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (2015): o896—o897. http://dx.doi.org/10.1107/s2056989015020265.

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In the title compound, 0.75C12H14ClNO2·0.25C12H14ClNO, which is an adduct comprising 0.75 4-hydroxypiperidin-1-yl or 0.25 4-piperidin-1-yl substituents on a common (4-chlorophenyl)methanone component; the dihedral angles between the benzene ring and the two piperidine rings are 51.6 (3) and 89.5 (7)°, respectively. The hydroxypiperidine ring is in a bisectional oriention (bi) with the phenyl ring. In the crystal, intermolecular O—H...O hydrogen bonds between the hydroxypiperidine group and the keto O atom lead to the formation of chains extending along thec- axis direction.

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Kantlehner, Willi, Markus Vettel, and Bernhard Eppinger. "Orthoamide und Iminiumsalze, LXXVI [1]. Ein weiterer Beitrag zur Chemie der Trialkoxyacetonitrile/ Orthoamides and Iminium Salts LXXVI [1]. A Further Contribution to the Chemistry of Trialkoxyacetonitriles." Zeitschrift für Naturforschung B 67, no. 4 (2012): 373–88. http://dx.doi.org/10.1515/znb-2012-0412.

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An improved procedure for the preparation of trimethoxyacetonitrile (3a) starting from trichloroacetonitrile and sodium methanolate is described. Carbanions, obtained by the action of sodium hydride on nitriles, ethyl acetate and methylketones, react with trialkoxyacetonitriles 3 to give α- imino-orthocarboxylic acid trialkylesters 12, 14 and 20, which form an equilibrium with the tautomeric enamines 13, 15 and 21. The enamines 21 react with N,N-dimethylformamide dimethylacetal (24) to give amidines 25 which are cyclized to pyridinium salts 28 and 29 on treatment with benzyl bromide and acetyl

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40

Prisyazhnyuk, Vladimir, Matthias Jachan, Irene Brüdgam, Reinhold Zimmer та Hans-Ulrich Reissig. "Addition of lithiated methoxyallene to aziridines – a novel access to enantiopure piperidine and β-amino acid derivatives". Collection of Czechoslovak Chemical Communications 74, № 7-8 (2009): 1069–80. http://dx.doi.org/10.1135/cccc2009012.

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Addition of lithiated methoxyallene to aziridine derivatives provided the expected primary addition products. The less substituted carbon of the aziridine ring was attacked selectively. The primary adducts could be converted to enantiopure piperidine derivatives or β-amino acid derivatives. The unexpected reactions lead to a tricyclic sulfonamide and to alkynyl-substituted aminoethers. The efficient two-step conversion of a piperidone derivative to a benzomorphan demonstrates the potential of this approach to biologically active compounds.

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Barlin, GB, SJ Ireland, TMT Nguyen, B. Kotecka, and KH Rieckmann. "Potential Antimalarials. XXI. Mannich Base Derivatives of 4-[7-Chloro(and 7-trifluoromethyl)quinolin-4-ylamino]phenols." Australian Journal of Chemistry 47, no. 8 (1994): 1553. http://dx.doi.org/10.1071/ch9941553.

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Syntheses are reported for 4-(7-chloroquinolin-4-ylamino)-2,6-bis(piperidin-1-ylmethyl)phenol (2) and its 3-fluoro and 3-piperidinyl derivatives. Some mono-Mannich analogues with 2-fluoro, 2-t-butyl and 3-trifluoromethyl substituents have also been prepared. In tests for antimalarial activity against the FC-27 and K-1 isolates of Plasmodium falciparum in vitro, compound (2) proved to be the most active (IC50 6.3-12.5 nM).

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42

Kafka, Stanislav, Jan Kytner, Alexandra Šilhánková, and Miloslav Ferles. "Hydroboration of 1-(5-hexenyl)piperidine and trans–1-(3-hexenyl)piperidine." Collection of Czechoslovak Chemical Communications 52, no. 8 (1987): 2035–46. http://dx.doi.org/10.1135/cccc19872035.

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1-(5-Hexenyl)piperidine (Ia) and trans-1-(3-hexenyl)piperidine (Ib) were hydroborated with tetrahydrofuran-borane, diborane in situ, 9-borabicyclo[3.3.1]nonane and triethylamine-borane. The hydroboration products were converted to 1-piperidinylhexanols IIa-IIe by hydrolysis with hydrochloric acid and subsequent oxidation with hydrogen peroxide in an alkaline medium. In addition to the alcohols IIa-IIe, the reaction also gave 1-hexylpiperidine (Ic). In the reactions with diborane in situ and triethylamine-borane, thermal isomerization of the hydroboration products was also studied. Hydroboratio

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Möhrle, H., and M. Jeandrée. "Reaktionsbeteiligung elektrophiler Funktionen bei der Dehydrierung 4-substituierter Piperidine / Participation of Electrophilic Groups with the Dehydrogenation of 4-Substituted Piperidines." Zeitschrift für Naturforschung B 55, no. 1 (2000): 74–85. http://dx.doi.org/10.1515/znb-2000-0113.

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Dehydrogenation of 2-(1-piperidinyl)-benzaldehydes 1-3 using mercury(II)-EDTA gen erated the lactams 4-6, indicating a reversible reaction of a carbinolamine intermediate with the formyl group. The yields and oxidation rates decreased by 4-substitution in the piperidine moiety.The 2-(1-piperidinyl)-acetophenones 11, 16-19 showed a similar behavior with mercury(II)-EDTA but gave rise to a product pattern. The trans-benzoquinolizidones 12, 20, 23, 26, 29 resulted from the cyclic iminium compounds reacting with the acetyl group as nucleophile. By another oxidation these species were partially tr

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44

Astaneh, H. R. Haghjoo, and E. O. Moradi Rufchahi. "Use of Nanocrystalline ZnO as an Efficient and Reusable Catalyst for a One-Pot, Three-Component Synthesis of 6-Chloro- and 5,7-Dichloro-4-Hydroxy-3-[Aryl (Piperidin-1-yl)Methyl]Quinolin-2(1H)-Ones in Water." Journal of Chemical Research 42, no. 2 (2018): 116–20. http://dx.doi.org/10.3184/174751918x15192990175864.

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A one-pot, green, efficient and facile procedure was applied for the preparation of a series of 4-hydroxy-3-[aryl(piperidin-1-yl)methyl] quinolin-2(1 H)-ones via the reaction of 6-chloro-4- hydroxyquinoline-2(1 H)-one 1 and/or 5,7-dichloro-4-hydroxyquinoline-2(1 H)-one 2, piperidine and aromatic aldehydes in water in the presence of nanocrystalline ZnO under reflux conditions. The desired products were obtained in satisfactory yields. The nanocrystalline ZnO can be separated and reused at least up to three times with almost the same catalytic activity.

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Goswami, Shailesh K., Lyall R. Hanton, C. John McAdam, Stephen C. Moratti, and Jim Simpson. "Structure and packing of aminoxyl and piperidinyl acrylamide monomers." Acta Crystallographica Section C Structural Chemistry 71, no. 10 (2015): 860–66. http://dx.doi.org/10.1107/s2053229615015946.

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The closely related title compounds, 4-acrylamido-2,2,6,6-tetramethylpiperidine-1-oxyl, C12H21N2O2, (I), andN-(2,2,6,6-tetramethylpiperidin-4-yl)acrylamide monohydrate, C12H22N2O·H2O, (II), are important monomers in the preparation of redox-active polymers. They comprise an acrylamide group of the usuals-cisconfiguration appended to a 2,2,6,6-tetramethyl-substituted piperidine-1-oxyl radical or a piperidinyl chair, respectively. The adjacent amide and piperidinyl H atoms are approximatelytransacross the C—N bond. The packing in (I) is dominated by N—H...O hydrogen bonds; these are supported by

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46

Salgado, Mateo M., Alejandro Manchado, Carlos T. Nieto, David Díez, and Narciso M. Garrido. "Asymmetric Synthesis of 2,3,6-Trisubstituted Piperidines via Baylis–Hillman Adducts and Lithium Amide through Domino Reaction." Synlett 31, no. 06 (2019): 600–604. http://dx.doi.org/10.1055/s-0039-1690990.

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A convenient asymmetric synthesis of methyl (2S,3S,6R)-6-(4-fluorophenyl)-2-(4-hydroxyphenyl)-piperidine-3-carboxylate is described, starting from Baylis–Hillman adducts. The route involves a domino process: allylic acetate rearrangement, stereoselective Ireland–Claisen rearrangement and asymmetric Michael addition, which provides a δ-amino acid derivative with full stereochemical control. A subsequent chemoselective transformation of one of the side-chain groups allows an effective cyclization leading to biologically interesting polysubstituted piperidines in which the 2,6-aryl groups could b

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Żesławska, Ewa, Justyna Kalinowska-Tłuścik, Wojciech Nitek, Henryk Marona, and Anna M. Waszkielewicz. "Influence of the position of the methyl substituent and N-oxide formation on the geometry and intermolecular interactions of 1-(phenoxyethyl)piperidin-4-ol derivatives." Acta Crystallographica Section C Structural Chemistry 76, no. 1 (2020): 30–36. http://dx.doi.org/10.1107/s2053229619015948.

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Aminoalkanol derivatives have attracted much interest in the field of medicinal chemistry as part of the search for new anticonvulsant drugs. In order to study the influence of the methyl substituent and N-oxide formation on the geometry of molecules and intermolecular interactions in their crystals, three new examples have been prepared and their crystal structures determined by X-ray diffraction. 1-[(2,6-Dimethylphenoxy)ethyl]piperidin-4-ol, C15H23NO2, 1, and 1-[(2,3-dimethylphenoxy)ethyl]piperidin-4-ol, C15H23NO2, 2, crystallize in the orthorhombic system (space groups P212121 and Pbca, res

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48

P.Badiger, Naveen, and I. M. Khazi. "Synthesis & Evaluation of Antitubercular Activity of Novel Mannich Bases of imidazo[2,1-b][1,3,4]thiadiazoles." Advanced Materials Research 816-817 (September 2013): 1197–201. http://dx.doi.org/10.4028/www.scientific.net/amr.816-817.1197.

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A series of 2-(4-methoxybenzyl)-6-aryl-5-pyrrolidin/piperidin/morpholin-1-ylmethyl-imidazo [2,1-[1,3, thiadiazoles (3a-e, 4a-e & 5a-e) were synthesized by Mannich reaction by condensing 2-(4-methoxybenzyl)-6-arylimidazo [2,1-[1,3,thiadiazoles with pyrrolidine, piperidine and morpholine. The title compounds were screened for antitubercular activity againstMycobacterium tuberculosisH37Rv using the BACTEC 460 radiometric assay. Mannich bases with pyrrolidine substitution were found to be most active antitubercular agents. It proves that as the ring size decreases it becomes much potent in its

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49

Modec, Barbara, Nina Podjed, and Nina Lah. "Beyond the Simple Copper(II) Coordination Chemistry with Quinaldinate and Secondary Amines." Molecules 25, no. 7 (2020): 1573. http://dx.doi.org/10.3390/molecules25071573.

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Copper(II) acetate has reacted in methanol with quinaldinic acid (quinoline-2-carboxylic acid) to form [Cu(quin)2(CH3OH)]∙CH3OH (1) (quin− = an anionic form of the acid) with quinaldinates bound in a bidentate chelating manner. In the air, complex 1 gives off methanol and binds water. The conversion was monitored by IR spectroscopy. The aqua complex has shown a facile substitution chemistry with alicyclic secondary amines, pyrrolidine (pyro), and morpholine (morph). trans-[Cu(quin)2(pyro)2] (2) and trans-[Cu(quin)2(morph)2] (4) were obtained in good yields. The morpholine system has produced a

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50

Yadav, Shiv Kumar, Chandra Kant Maurya, Pradeep Kumar Gupta, Ajai Kumar Jain, Kumaran Ganesan, and Rahul Bhattacharya. "Synthesis and biological evaluation of some novel 1-substituted fentanyl analogs in Swiss albino mice." Interdisciplinary Toxicology 7, no. 2 (2014): 93–102. http://dx.doi.org/10.2478/intox-2014-0013.

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ABSTRACT Fentanyl [N-(1-phenethyl-4-piperidinyl)propionanilide] is a potent opioid analgesic agent, but a has narrow therapeutic index. We reported earlier on the synthesis and bioefficacy of fentanyl and its 1-substituted analogs (1-4) in mice. Here we report the synthesis and biological evaluation of four additional analogs, viz. N-isopropyl-3-(4-(N-phenylpropionamido)piperidin-1-yl)propanamide (5), N-tbutyl- 3-(4-(N-phenylpropionamido)piperidin-1-yl)propanamide (6), isopropyl 2-[4-(N-phenylpropionamido)piperidin-1-yl]propionate (7) and t-butyl 2-[4-(N-phenylpropionamido)piperidin-1-yl]propi

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