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Journal articles on the topic 'Piperidine synthesis'

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Published: 4 June 2021

Last updated: 2 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

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

Mill, Sibel, and Claude Hootelé. "A revised structure for the piperidine alkaloid andrachamine." Canadian Journal of Chemistry 74, no. 12 (1996): 2434–43. http://dx.doi.org/10.1139/v96-272.

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A new method for the synthesis of trans-2,6-disubstituted piperidine derivatives is described. The transformation of cyclic α-methoxycarbamates 5 and 6 affords trans ketones 17 and 18. The synthesis of diols 1–4 from 17 and 18 has shown that the structure proposed in the literature for the piperidine alkaloid andrachamine is incorrect. A reexamination of the original spectral data of this alkaloid suggested that it is a meso 2,6-disubstituted piperidine derivative. Unambiguous syntheses of 23 and 24 and comparison with a sample of andrachamine have established that this alkaloid possesses stru

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11

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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12

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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13

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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14

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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15

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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16

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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17

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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18

Sengoku, Tetsuya, Jolanta Wierzejska, Masaki Takahashi, and Hidemi Yoda. "Evolution of the Total Syntheses of Batzellasides the First Marine Piperidine Iminosugar." Natural Product Communications 8, no. 7 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800729.

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Batzellasides A-C are C-alkylated piperidine iminosugars isolated from a sponge Batzella sp. The first total synthesis of (+)-batzellaside B was achieved by employing a chiral pool approach starting from L-arabinose for the construction of a piperidine ring system. Subsequently a practical second-generation synthesis was developed by utilizing a Sharpless asymmetric dihydroxylation for the preparation of the common piperidine intermediate elaborated in the first-generation synthesis. The overall yield of batzellaside B was improved to 3.3% by introducing the exocyclic C8 stereocenter via facia

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19

Logvinenko, Ivan G., Violetta G. Dolovanyuk та Ivan S. Kondratov. "The preparative synthetic approach to 4-(triﬂuoromethoxy)piperidine and 4-(triﬂuoromethoxymethyl)piperidine". Journal of Organic and Pharmaceutical Chemistry 19, № 1(73) (2021): 3–9. http://dx.doi.org/10.24959/ophcj.21.222669.

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Aim. To develop a convenient synthetic approach for the preparation of multigram amounts of 4-(triﬂuoromethoxy)-piperidine and 4-(triﬂuoromethoxymethyl)piperidine – promising building blocks for medicinal chemistry.Results and discussion. 4-(Triﬂuoromethoxy)piperidine (8.4 g) and 4-(triﬂuoromethoxymethyl)piperidine (12.9 g) were synthesized in 5 stages starting from 4-hydroxypiperidine (the overall yield 40 %) and 4-(hydroxymethyl)piperidine (the overall yield 13.5 %), respectively.Experimental part. The first stage of the synthetic strategy was acylation of 4-hydroxypiperidine with benzoyl ch

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20

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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21

Armbrecht, Michael, Walter Maringgele, Anton Meller, Mathias Noltemeyer, and George M. Sheldrick. "Synthesen und Eigenschaften von Piperidin-N-oxyboranen / Synthesis and Properties of Piperidine-N-oxyboranes." Zeitschrift für Naturforschung B 40, no. 9 (1985): 1113–22. http://dx.doi.org/10.1515/znb-1985-0904.

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Piperidine-N-oxyboranes and 2,2,6,6-Tetramethylpiperidine-N-oxyboranes have been prepared starting from halogenoboranes by three methods: a) By reaction with N-hydroxypiperidine and triethylamine; b) by cleavage of the Si -O-bond in piperidine-N-oxy-trimethylsilanes and c) by reaction with metallated piperidine-N-oxy compounds. Diboryloxides and diborylamides, resp., are obtained upon reaction of piperidine-N-oxybrom oboranes with hexamethyldisiloxane and hexamethyldisilazane. Steric influences upon reactivity and spectroscopic properties are discussed. The compounds are characterized by eleme

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22

Bonandi, Elisa, Giada Tedesco, Dario Perdicchia, and Daniele Passarella. "Total Synthesis of (–)-Anaferine: A Further Ramification in a Diversity-Oriented Approach." Molecules 25, no. 5 (2020): 1057. http://dx.doi.org/10.3390/molecules25051057.

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The piperidine ring is a widespread motif in several natural bioactive alkaloids of both vegetal and marine origin. In the last years, a diversity-oriented synthetic (DOS) approach, aimed at the generation of a library of piperidine-based derivatives, was developed in our research group, employing commercially available 2-piperidine ethanol as a versatile precursor. Here, we report the exploration of another ramification of our DOS approach, that led us to the stereoselective total synthesis of (–)-anaferine, a bis-piperidine alkaloid present in Withania somnifera extract. This natural product

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23

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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24

Enders, Dieter, and Christoph Thiebes. "Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids." Pure and Applied Chemistry 73, no. 3 (2001): 573–78. http://dx.doi.org/10.1351/pac200173030573.

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Recent advances in the diastereo- and enantioselective synthesis of piperidine, pyrrolidine, and indolizidine alkaloids, based on the highly stereoselective 1,2-addition to the CN double bond of chiral aldehyde-SAMP/RAMP hydrazones, are described. The enantioselective syntheses of the pyrrolidine alkaloids bgugaine and (2S,12¢R)-2-(12¢-aminotridecyl)-pyrrolidine, a defense alkaloid of the Mexican bean beetle are reported. Furthermore, the SAMP/RAMP-hydrazone method was applied to the syntheses of two 5,8-disubstituted indolizidine alkaloids that have been extracted from neotropical poison-dart

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25

Kliger, G. A., O. A. Lesik, A. I. Mikaya, et al. "Piperidine-modified fischer-tropsch synthesis." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 40, no. 2 (1991): 435–38. http://dx.doi.org/10.1007/bf00965446.

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26

Šindelář, Karel, Jiří Holubek, Jiří Schlanger, Antonín Dlabač, Martin Valchář, and Miroslav Protiva. "Synthesis of spiro(piperidine-4,6'-dibenz[b,e]-1,4-oxathiepin) and its 1-methyl derivative as potential antidepressant agents." Collection of Czechoslovak Chemical Communications 50, no. 2 (1985): 503–9. http://dx.doi.org/10.1135/cccc19850503.

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Starting from 2-chloronitrobenzene and 2-fluorothiophenol, the synthesis of 2-bromo-2'-fluorodiphenyl sulfide (X) was carried out in three steps. The product was converted to the Grignard reagent which reacted with 1-ethoxycarbonyl-4-piperidone and gave the alcohol XIII. Cyclization of this compound with sodium hydride in dimethylformamide afforded 1-ethoxycarbonylspiro(piperidine-4,6'-dibenz[b,e]-1,4-oxathiepin) (V) which was hydrolyzed to the title compound IV. Reduction of compound V with sodium dihydridobis(2-methoxyethoxy)aluminate afforded the 1-methyl derivative III which exhibited anti

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27

Pareek, Veena, Pradeep K. Paliwal, and Shubha Jain. "SYNTHESIS AND CHARACTERIZATION OF SOME BENZOTHIAZOLOPYRAZOLINE DERIVATIVES." International Journal of Engineering Technologies and Management Research 4, no. 12 (2020): 94–97. http://dx.doi.org/10.29121/ijetmr.v4.i12.2017.598.

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A new route for the synthesis of benzothiazolopyrazoline derivatives has been developed using various chalcone derivatives and 2-hydrazinobenzothiazole and piperidine catalyst. The product obtained in shorter reaction times and piperidine behaves as good catalyst for the cycloaddition rof chalcone and 2-hydrazinobenzothiazole. The reaction carried out in aqueous-ethanol medium at reflux condition and product obtained in high yield.

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28

Suzuki, Kana, Yasunao Hattori, Atsushi Kawamura, and Hidefumi Makabe. "Synthesis of (+)-solenopsin via Pd-catalyzed N-alkylation and cyclization." Bioscience, Biotechnology, and Biochemistry 85, no. 2 (2021): 223–27. http://dx.doi.org/10.1093/bbb/zbaa014.

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ABSTRACT Synthesis of (+)-solenopsin, a 2,6-disubstituted piperidine alkaloid, isolated from fire ants (Solenopsis), was achieved. Stereoselective construction of trans-2,6-piperidine ring moiety was performed using palladium-catalyzed cyclization. Chain elongation using Grubbs 2nd catalyst followed by the reduction of double bond and the deprotection of the Cbz group afforded (+)-solenopsin.

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29

Stumpf, Andreas, Frédéric St-Jean, David Lao, Zhigang Ken Cheng, Remy Angelaud, and Francis Gosselin. "Practical Early Development Synthesis of Nav1.7 Inhibitor GDC-0310." Synthesis 52, no. 22 (2020): 3406–14. http://dx.doi.org/10.1055/s-0040-1707859.

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The concise early development route to the Nav1.7 inhibitor GDC-0310 is described. The active pharmaceutical ingredient (API) contains one stereocenter, which was obtained with high enantiomeric excess (>99:1) by using an SN2 displacement approach to connect two intermediates: a chiral benzyl alcohol and a piperidine. The synthesis of the piperidine building block proceeded via a regioselective SNAr reaction on 1-chloro-2,4-difluorobenzene by N-Boc-4-piperidinemethanol, followed by installation of the methyl ester group by electrophilic aromatic bromination and a palladium-catalyzed alkoxyc

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30

Zhao, Hui, Wen-Bo Zhao, Jian-She Zhu, Yue-Mei Jia, and Chu-Yi Yu. "An Efficient Synthesis of Aldohexose-Derived Piperidine Nitrones: Precursors of Piperidine Iminosugars." Molecules 18, no. 5 (2013): 6021–34. http://dx.doi.org/10.3390/molecules18056021.

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31

McAdam, C. John, Joy L. Morgan, R. Eva Murray, Brian H. Robinson, and Jim Simpson. "Synthesis and Fluorescence Properties of New Enaminenaphthalimides." Australian Journal of Chemistry 57, no. 6 (2004): 525. http://dx.doi.org/10.1071/ch03285.

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The first 4-enamine-N-methyl-1,8-naphthalimides (amine = piperidine, pyrrolidine, morpholine, Prn2NH, Pri2NH) are reported. The X-ray crystal structure of the piperidine derivative confirmed the E-stereochemistry and showed strong Π–Π stacking in the unit cell. The enamines are strongly fluorescent and quantum yields do not vary with the pKb of the amine. The solvent dependence of λ abs and λ flu is consistent with significant charge separation in the excited state.

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32

Cossy, J., C. Poitevin, D. Gomez Pardo, J. L. Peglion, and A. Dessinges. "Synthesis of Spiro[benzazepine-2,4‘-piperidine]." Journal of Organic Chemistry 63, no. 13 (1998): 4554–57. http://dx.doi.org/10.1021/jo9803986.

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33

Kranke, Birgit, and Horst Kunz. "Stereoselective synthesis of chiral piperidine derivatives employing arabinopyranosylamine as the carbohydrate auxiliary." Canadian Journal of Chemistry 84, no. 4 (2006): 625–41. http://dx.doi.org/10.1139/v06-060.

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Stereoselective synthesis of 2-substituted dehydropiperidinones and their further transformation to variously disubstituted piperidine derivatives was achieved employing D-arabinopyranosylamine as the stereodifferentiating carbohydrate auxiliary. A domino MannichMichael reaction of 1-methoxy-3-(trimethylsiloxy)butadiene (Danishefsky's diene) with O-pivaloylated arbinosylaldimines furnished N-arabinosyl dehydropiperidinones in high diastereoselectivity. Subsequent conjugate cuprate addition gave 2,6-cis-substituted piperidinones, while enolate alkylation furnished 2,3-trans-substituted dehydro

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34

Laras, Younes, Nicolas Pietrancosta, Vincent Moret, et al. "Synthesis of New Substituted 4,5-Dihydro-3H-spiro[1,5]-benzoxazepine-2,4′-piperidine and Biological Properties." Australian Journal of Chemistry 59, no. 11 (2006): 812. http://dx.doi.org/10.1071/ch06318.

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The reduction of substituted spiro-piperidinyl chromanone oximes with DIBAH reagents has been known to afford the corresponding substituted 4,5-dihydro-3H-spiro[1,5]-benzoxazepine-2,4′-piperidine. The position and electronic effects of the substituents on the aryl moiety control the observed rearrangement. Spiro-benzoxazepine analogue 5j represents a key intermediate for the creation of a library of diverse potential bioactive drugs. With three functional groups that could be selectively and orthogonally protected, many different substituents can be introduced. The obtained analogues were assa

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35

Kiricojevic, Vesna, Milovan Ivanovic, I. V. Micovic, J. B. Djordjevic, Goran Roglic, and Ljiljana Dosen-Micovic. "An optimized synthesis of a key pharmaceutical intermediate methyl 4-[(1-oxopropyl)phenylamino]piperidine-4-carboxylate." Journal of the Serbian Chemical Society 67, no. 12 (2002): 793–802. http://dx.doi.org/10.2298/jsc0212793k.

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An efficient synthesis of methyl 4-[(1-oxopropyl)phenylamino]piperidine-4-carboxylate (7) has been developed starting from 1-benzylpiperidin-4-one (1). The compound is a key intermediate in the synthesis of new generation, highly active narcotic analgesics, such as remifintanil, as well as the novel classes of fentanyl analogues. An optimized Strecker-type condensation of piperidone 1 with aniline and HCN yielded the anilino-nitrile 2(?90%) which, upon selective hydrolysis with conc. H2SO4, gave the anilino-amide 3.After vigorous basic hydrolysis of 3, followed by acidification and successive

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36

OLIVEIRA, MAILCAR F., TELMA L. G. LEMOS, MARCOS C. DE MATTOS, TACIANA A. SEGUNDO, GILVANDETE M. P. SANTIAGO, and RAIMUNDO BRAZ-FILHO. "New enamine derivatives of lapachol and biological activity." Anais da Academia Brasileira de Ciências 74, no. 2 (2002): 211–21. http://dx.doi.org/10.1590/s0001-37652002000200004.

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A convenient synthesis of the new enamine derivatives 2-(4-morpholinyl)-3-(3-methyl-2-butenyl)-1,4-naphthalenedione, 2-(1-piperidinyl)-3-(3-methyl-2-butenyl)-1,4-naphtalenedione and 2-(1-pyrrolidinyl)-3-(3-methyl-2-butenyl)-1,4-naphthalenedione was carried out from natural 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione (lapachol) and morpholine, piperidine and pyrrolidine. The structures of the products were established mainly by NMR analysis, including 2D experiments. Biological activities of these products were evaluated against Artemia salina, Aedes aegypti and cytotoxicity using A54

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37

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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38

Lin, G., K. K. Midha, and E. M. Hawes. "Synthesis of the piperidinone metabolites of piperidine type phenothiazine antipsychotic drugsviaruthenium tetroxide oxidation." Journal of Heterocyclic Chemistry 28, no. 2 (1991): 215–19. http://dx.doi.org/10.1002/jhet.5570280202.

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39

Raji Reddy, Chada, Bellamkonda Latha, Kamalkishor Warudikar, and Kiran Kumar Singarapu. "Total synthesis of a piperidine alkaloid, microcosamine A." Organic & Biomolecular Chemistry 14, no. 1 (2016): 251–58. http://dx.doi.org/10.1039/c5ob02085a.

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40

Srivastava, Nikhil, Lingamurthy Macha, and Hyun-Joon Ha. "Stereoselective synthesis of 2,6-disubstituted piperidine alkaloids." Organic & Biomolecular Chemistry 18, no. 29 (2020): 5493–512. http://dx.doi.org/10.1039/d0ob00918k.

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The synthetic methods to build the 2,6-disubstituted piperidine structural motif were described focusing on stereochemical control of two substituents at C2 and C6 with specific examples of natural products.

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41

Darwish, Elham S., Mahmoud A. Abdelrahman, and Abdellatif M. Salaheldin. "Enamines in Heterocyclic Synthesis: A Novel Simple and Efficient Route to Condensed Pyridazines." Zeitschrift für Naturforschung B 66, no. 6 (2011): 597–602. http://dx.doi.org/10.1515/znb-2011-0607.

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An efficient and easy preparation of enamine derivatives, via active methyl and methylene compounds by in situ-generated 1-(diethoxymethyl)piperidine, produced from the mixture of triethyl orthoformate/piperidine/DMF, are described. Some new pyridazinone derivatives have been synthesized from the reaction of enamines with hydrazine hydrate and cyanoacid hydrazide.

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42

Sun, Pengcheng, Wenli Tang, Yu Huang, and Bi-Huang Hu. "Improved Fmoc Solid-Phase Peptide Synthesis of Oxytocin with High Bioactivity." Synlett 28, no. 14 (2017): 1780–84. http://dx.doi.org/10.1055/s-0036-1589037.

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We described here the synthesis of oxytocin by an improved Fmoc solid-phase peptide synthesis (SPPS) method with a Rink-Amide resin as the solid support, HBTU as the coupling reagent, Fmoc-protected amino acids as the building blocks, and piperazine for Fmoc removal as a substitute for the standard reagent piperidine. Unlike previously reported syntheses, the removal of the S-Acm protecting group of Cys and cyclization forming the disulfide bond were carried out by using iodine on the resin with the fully protected peptide chains. Finally, a crude oxytocin with a purity of 92% was obtained by

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43

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 (2012): 0389. http://dx.doi.org/10.5560/znb.2012.67b0389.

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44

Vinaya, Kambappa, Chandagirikoppal V. Kavitha, Siddappa Chandrappa, Doddakunche S. Prasanna, Sathees C. Raghavan, and Kanchugarakoppal S. Rangappa. "Synthesis and Antileukemic Activity of Novel 4-(3-(Piperidin-4-yl) Propyl)Piperidine Derivatives." Chemical Biology & Drug Design 78, no. 4 (2011): 622–30. http://dx.doi.org/10.1111/j.1747-0285.2011.01184.x.

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45

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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46

Driessens, Frank, and ClaUDE Hootelé. "Sedum alkaloids. XI. Synthesis of sedinone and sedacrine by application of anodic oxidation." Canadian Journal of Chemistry 69, no. 2 (1991): 211–17. http://dx.doi.org/10.1139/v91-034.

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α-Methoxycarbamate 12, synthetic precursor of the 2,6-disubstituted alkaloids of Sedum acre, was obtained in high yield from 2-phenacylpiperidine 5; the key step of the synthesis rests on the anodic methoxylation, which allows the functionalization of carbon 6. Nucleophilic substitution of the methoxy group by an acetonyl chain leads, after the required transformations, to sedinone 23. Bromomethoxylation of the enecarbamate 19 followed by dehydrohalogenation and nucleophilic substitution of the methoxy group leads to sedacrine 33. In both cases, the nucleophilic substitution of the methoxy gro

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47

Trost, Barry M., Anthony B. Pinkerton, and Doris Kremzow. "A Ruthenium-Catalyzed Pyrrolidine and Piperidine Synthesis." Journal of the American Chemical Society 122, no. 48 (2000): 12007–8. http://dx.doi.org/10.1021/ja003168t.

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48

JAING, Fuxiang, Qiaozhen LIU, Guo WANG, and Heru CHEN. "Synthesis of Piperidine Derivatives from 1,5-Diols." Acta Agronomica Sinica 30, no. 7 (2013): 769. http://dx.doi.org/10.3724/sp.j.1095.2013.20516.

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49

Adriaenssens, Louis V., Carolyn A. Austin, Mairi Gibson, David Smith, and Richard C. Hartley. "Stereodivergent Diversity Oriented Synthesis of Piperidine Alkaloids." European Journal of Organic Chemistry 2006, no. 22 (2006): 4998–5001. http://dx.doi.org/10.1002/ejoc.200600744.

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50

Saikia, Anil K., Kiran Indukuri, and Jagadish Das. "Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D." Org. Biomol. Chem. 12, no. 36 (2014): 7026–35. http://dx.doi.org/10.1039/c4ob01130a.

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A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (±)-epi-indolizidine 167B and 209D.

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