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Journal articles on the topic 'Piperidine ring'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

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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2

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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3

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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4

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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5

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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6

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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7

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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8

Kiss, Loránd, Melinda Nonn, Lamiaa Ouchakour, and Attila M. Remete. "Application of Oxidative Ring Opening/Ring Closing by Reductive Amination Protocol for the Stereocontrolled Synthesis of Functionalized Azaheterocycles." Synlett 33, no. 04 (2021): 307–28. http://dx.doi.org/10.1055/s-0040-1719850.

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AbstractThe current Account gives an insight into the synthesis of some N-heterocyclic β-amino acid derivatives and various functionalized saturated azaheterocycles accessed from substituted cycloalkenes via ring C=C bond oxidative cleavage followed by ring closing across double reductive amination. The ring-cleavage protocol has been accomplished according to two common approaches: a) Os-catalyzed dihydroxylation/NaIO4 vicinal diol oxidation and b) ozonolysis. A comparative study on these methodologies has been investigated. Due to the everincreasing relevance of organofluorine chemistry in d

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9

Vinuchakkaravarthy, T., R. Sivakumar, T. Srinivasan, V. Thanikachalam, and D. Velmurugan. "(E)-3-Isopropyl-1-methyl-2,6-diphenylpiperidin-4-oneO-nicotinoyl oxime." Acta Crystallographica Section E Structure Reports Online 70, no. 5 (2014): o551. http://dx.doi.org/10.1107/s1600536814007363.

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In the title compound, C27H29N3O2, the piperidine ring exists in a chair conformation with an equatorial orientation of the phenyl and methyl substituents. The C—C=N bond angles are significantly different [119.1 (2) and 127.2 (2)°]. The phenyl rings are inclined to one another by 44.90 (14)°, and by 80.85 (13) and 79.62 (12)° to the mean plane of the piperidine ring. The terminal pyridine ring is inclined to the piperidine ring mean plane by 74.79 (15)°. In the crystal, molecules are linked by C—H...π interactions, forming a three-dimensional network.

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10

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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11

Ullah, Nisar, and Helen Stoeckli-Evans. "8-{1-[(4′-Fluoro-[1,1′-biphenyl]-4-yl)methyl]piperidin-4-yl}-3,4-dihydroquinolin-2(1H)-one chloroform 0.25-solvate." Acta Crystallographica Section E Structure Reports Online 70, no. 2 (2014): o103—o104. http://dx.doi.org/10.1107/s160053681303448x.

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In the asymmetric unit of the title compound, C27H27FN2O·0.25CHCl3, there are two independent molecules (AandB) together with a partially disordered chloroform molecule situated about an inversion center. The conformation of the two molecules is very similar. The bridging piperidine rings each have a chair conformation while the piperidin-2-one rings of the quinoline moiety have screw-boat conformations. The benzene rings of the biphenyl moiety are inclined to one another by 26.37 (4) and 23.75 (15)° in moleculesAandB, respectively. The mean plane of the central piperidine ring [r.m.s. deviati

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12

Lakshminarayana, B. N., J. Shashidhara Prasad, C. R. Gnanendra, M. A. Sridhar, and D. Chenne Gowda. "1-(2-Chloroacetyl)-3-methyl-2,6-bis(3,4,5-trimethoxyphenyl)piperidine-4-one." Acta Crystallographica Section E Structure Reports Online 65, no. 6 (2009): o1237. http://dx.doi.org/10.1107/s1600536809015864.

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In the crystal structure of the title compound, C26H32ClNO8, the piperidine ring is in a twist-chair conformation, with puckering parametersQ= 0.655 (4) Å, θ = 93.1 (1) and φ = 254.4 (3)°. TheorthoC atoms of the piperidine ring deviate from the plane defined by the remaining ring atoms by 0.380 (3) and −0.250 (3) Å.

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13

Sabancılar, İlhan, Murat Aydemir, and Seçkin Kaya. "Characteristics of the biological activities of the piperidine complex: an anticancer and antioxidant investigation." Northwestern Medical Journal 5, no. 2 (2025): 112–21. https://doi.org/10.54307/2025.nwmj.142.

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Aim: To determine the anticancer and antioxidant activity levels of the synthesized heterocyclic molecule named 1-benzyl-1-(2- methyl-3-oxo-3-(p-tolyl)propyl) piperidin-1-ium chloride. Methods: The molecule 1-benzyl-1-(2-methyl-3-oxo-3-(p-tolyl) propyl)piperidin-1-ium chloride was synthesized solvent-free via microwave synthesis. Piperidine purification involved dichloromethane extraction with 2 M HCl, followed by 5% NaHCO3 and precipitation with n-hexane. Anticancer activity on A549 lung cancer cells was assessed using the MTT assay. Antioxidant activity was evaluated by DPPH and CUPRAC metho

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14

Raghuvarman, B., R. Sivakumar, K. Gokula Krishnan, V. Thanikachalam, and S. Aravindhan. "(E)-1,3-Dimethyl-2,6-diphenylpiperidin-4-oneO-(phenoxycarbonyl)oxime." Acta Crystallographica Section E Structure Reports Online 70, no. 6 (2014): o713. http://dx.doi.org/10.1107/s1600536814010526.

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The title piperidine derivative, C26H26N2O3, has anEconformation about the N=C bond. The piperidine ring has a chair conformation and its mean plane is almost perpendicular to the attached phenyl rings, making dihedral angles of 87.47 (9) and 87.34 (8)°. The planes of these two phenyl rings are inclined to one another by 60.38 (9)°. The plane of the terminal phenyl ring is tilted at an angle of 32.79 (9)° to the mean plane of the piperidine ring. The molecular conformation is stabilized by two intramolecular C—H...O contacts. There are no significant intermolecular interactions in the crystal.

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15

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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16

Ahmad, Manzoor, Shamsher Ali, Farzana Shaheen, Shazia Anjum, and M. Iqbal Choudhary. "14-Acetyl-20-ethyl-1,8-dihydroxy-16,18-dimethoxylycoctonine." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (2006): o1428—o1430. http://dx.doi.org/10.1107/s1600536806008944.

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The title compound (C25H39NO6), a polycyclic diterpenoid alkaloid, has been isolated from Delphinium roylei Munz. Two cis-fused ring junctions are observed between cyclohexane A and piperidine E rings and between cyclohexane B and cyclopentane C rings. Two trans-fused ring junctions involve cyclohexane A and cyclopentane B rings and also piperidine E and cyclopentane F rings. Cyclopentane ring F is in a twist conformation, while the other cyclopentane ring, C, forms an envelope conformation. Piperidine ring E is in a chair conformation, the two cyclohexane rings A and B adopt twist–boat confor

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17

Revathi, B. K., D. Reuben Jonathan, K. Kalai Sevi, K. Dhanalakshmi, and G. Usha. "Crystal structure of [4-(chloromethyl)phenyl](4-hydroxypiperidin-1-yl)methanone." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (2015): o703—o704. http://dx.doi.org/10.1107/s2056989015016096.

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The title compound, C13H16ClNO2, crystallized with two independent molecules in the asymmetric unit (AandB). The piperidinol ring in moleculeBis disordered over two positions with a site occupancy ratio of 0.667 (5):0.333 (5). In both molecules these rings have a chair conformation, including the minor component in moleculeB. Their mean planes are inclined to the benzene ring by 45.57 (13)° in moleculeA, and by 50.5 (4)° for the major component of the piperidine ring in moleculeB. In the crystal, the individual molecules are linked by O—H...O hydrogen bonds, forming chains ofAandBmolecules alo

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18

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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19

Shreevidhyaa Suressh, V., B. K. Revathi, S. Abdul Basheer, S. Ponnuswamy, and G. Usha. "Crystal structure of 2-chloro-1-(3-ethyl-2,6-diphenylpiperidin-1-yl)ethanone." Acta Crystallographica Section E Crystallographic Communications 71, no. 2 (2015): o122. http://dx.doi.org/10.1107/s2056989015000444.

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In the racemic title compound, C21H24ClNO, the dihedral angle between the planes of the benzene rings is 86.52 (14)° and those between the benzene rings and the piperidine ring are 61.66 (14) and 86.39 (14)°. The piperidine ring adopts a twisted boat conformation. No directional interactions could be detected in the crystal.

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20

Kamaraj, A., S. Ranjith, R. Rajkumar, G. Mohanraj, and K. Krishnasamy. "Crystal structure of 1-cyclopropanecarbonyl-3-methyl-2,6-di-p-tolylpiperidin-4-one." Acta Crystallographica Section E Structure Reports Online 70, no. 9 (2014): o1056—o1057. http://dx.doi.org/10.1107/s1600536814018546.

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The title compound, C24H27NO2, crystallizes with two independent molecules (AandB) in the asymmetric unit. The two molecules have very similar conformations and each exhibits an intramolecular C—H...π interaction. The central piperidine rings adopt boat conformations and thep-tolyl rings are inclined to the mean plane of the piperidine ring by 71.21 (11) and 89.86 (12)° in moleculeAand by 68.01 (12) and 89.33 (12)° in moleculeB. The cyclopropanecarbonyl group is oriented at an angle of 68.5 (2)° with respect to the mean plane of the piperidine ring in moleculeAand 66.2 (2)° in moleculeB. In th

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21

Sathya, S., K. Prathebha, G. Usha, S. Abdul Basheer, and S. Ponnuswamy. "3,5-Dimethyl-2,6-diphenylpiperidine." Acta Crystallographica Section E Structure Reports Online 70, no. 4 (2014): o404. http://dx.doi.org/10.1107/s160053681400470x.

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In the title compound, C19H23N, the piperidine ring has a chair conformation. The phenyl rings are inclined to one another by 52.76 (16)°. One of the methyl substituents on the piperidine ring is axial while the other is equatorial, like the phenyl rings. In the crystal, molecules are linkedviaC—H...π interactions, forming zigzag chains along [001].

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22

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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23

Shalaby, ElSayed M., Aisha M. Moustafa, Adel S. Girgis, and Aida M. ElShaabiny. "Crystal Structures of Ethyl 4-(4-Florophenyl)-6-phenyl-2-substituted-3-pyridinecarboxylates." Journal of Crystallography 2014 (May 4, 2014): 1–7. http://dx.doi.org/10.1155/2014/148741.

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Three substituted pyridinecarboxylates were synthesized; (I) ethyl 2-bromo-4-4(fluorophenyl)-6-phenyl-3-pyridinecarboxylate, C20H15BrFNO2, (II) ethyl 4-(4-fluorophenyl)-2-(4-morpholinyl)-6-phenyl-3-pyridinecarboxylate, C24H23FN2O3, and (III) ethyl 4-(4-fluorophenyl)-6-phenyl-2-(1-piperidinyl)-3-pyridinecarboxylate, C25H25FN2O2. It was found that compound (I) belongs to the orthorhombic system with space group P212121, compound (II) to the monoclinic system with space group P21/c, and compound (III) to the monoclinic system with space group C2/c. The morpholine ring in (II) and piperidine ring

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24

Kumar, K. Mahesh, M. Vinduvahini, N. M. Mahabhaleshwaraiah, O. Kotresh, and H. C. Devarajegowda. "(6-Methoxy-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodithioate." Acta Crystallographica Section E Structure Reports Online 69, no. 11 (2013): o1683. http://dx.doi.org/10.1107/s1600536813028432.

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In the title compound, C17H19NO3S2, the maximum deviation of atoms in the 2H-chromene ring system is 0.0097 (14) Å and the piperidine ring adopts a chair conformation. The dihedral angle between the 2H-chromene ring and the piperidine ring (all atoms) is 87.59 (8)°. In the crystal, inversion dimers linked by pairs of C—H...O interactions generateR22(22) loops. Further C—H...O hydrogen bonds link the dimers into [110] chains and weak aromatic π–π stacking [shortest centroid–centroid distance = 3.824 (8) Å] is also observed.

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25

Prathebha, K., D. Reuben Jonathan, S. Sathya, R. Vasanthi, and G. Usha. "Crystal structure of 4-methyl-N-{[1-(4-methylbenzoyl)piperidin-4-yl]methyl}benzamide." Acta Crystallographica Section E Structure Reports Online 70, no. 11 (2014): o1157. http://dx.doi.org/10.1107/s1600536814021965.

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In the title compound, C22H27N2O2, the piperidine ring adopts a half-chair conformation with the benzene rings inclined in atransorientation with respect to the piperidine ring [dihedral angle between the benzene rings = 89.1 (1)°]. In the crystal, a three-centre asymmetric N—H...O/C—H...O hydrogen-bonding interaction leads to the formation of chains extending along thea-axis direction.

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26

Ghabbour, Hazem A., Adnan A. Kadi, Hussein I. El-Subbagh, Tze Shyang Chia, and Hoong-Kun Fun. "N-[4-(4-Bromophenyl)thiazol-2-yl]-4-(piperidin-1-yl)butanamide." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1665. http://dx.doi.org/10.1107/s1600536812019204.

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In the title compound, C18H22BrN3OS, the piperidine ring adopts a chair conformation. The mean plane of the thiazole ring forms dihedral angles of 23.97 (10) and 75.82 (10)° with the mean planes of its adjacent benzene and piperidine rings, respectively. An intramolecular N—H...N hydrogen bond generates an S(7) ring motif in the molecule. In the crystal, no significant intermoelcular hydrogen bonds are observed, but a weak π–π interaction with a centroid–centroid distance of 3.8855 (13) Å occurs.

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27

Goldberg, Joel S. "Stereochemical Basis for a Unified Structure Activity Theory of Aromatic and Heterocyclic Rings in Selected Opioids and Opioid Peptides." Perspectives in Medicinal Chemistry 4 (January 2010): PMC.S3898. http://dx.doi.org/10.4137/pmc.s3898.

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This paper presents a novel unified theory of the structure activity relationship of opioids and opioid peptides. It is hypothesized that a virtual or known heterocyclic ring exists in all opioids which have activity in humans, and this ring occupies relative to the aromatic ring of the drug, approximately the same plane in space as the piperidine ring of morphine. Since the rings of morphine are rigid, and the aromatic and piperidine rings are critical structural components for morphine's analgesic properties, the rigid morphine molecule allows for approximations of the aromatic and heterocyc

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28

Inglebert, S. Antony, Jayabal Kamalraja, K. Sethusankar, and Gnanasambandam Vasuki. "2-Amino-6-(piperidin-1-yl)-4-p-tolylpyridine-3,5-dicarbonitrile." Acta Crystallographica Section E Structure Reports Online 69, no. 12 (2013): o1807. http://dx.doi.org/10.1107/s1600536813030845.

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In the title compound, C19H19N5, the piperidine ring adopts a chair conformation. The pyridine ring is essentially planar, with a maximum deviation of 0.039 (2) Å for a C atom substituted with a carbonitrile group. The mean plane of the central pyridine ring makes the dihedral angles of 37.90 (14) and 56.10 (12)° with the piperidine and benzene rings, respectively. In the crystal, molecules are linkedviaN—H...N and C—H...N hydrogen bonds, forming chains along [101], and enclosingR22(17) ring motifs. The chains are linked by further C—H...N hydrogen bonds, forming two-dimensional networks lying

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29

Roopashree, K. R., T. G. Meenakshi, K. Mahesh Kumar, O. Kotresh, and H. C. Devarajegowda. "Crystal structure of (7-methyl-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodithioate." Acta Crystallographica Section E Crystallographic Communications 71, no. 8 (2015): o606—o607. http://dx.doi.org/10.1107/s2056989015013699.

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In the title compound, C17H19NO2S2, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.0383 (28) Å, and the piperidine ring adopts a chair conformation. The 2H-chromene ring makes dihedral angles of 32.89 (16) and 67.33 (8)°, respectively, with the mean planes of the piperidine ring and the carbodithioate group. In the crystal, C—H...O and weak C—H...S hydrogen bonds link the molecules into chains along [001]. The crystal structure also features C—H...π and π–π interactions, with a centroid–centroid distance of 3.7097 (17) Å.

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30

Ullah, Nisar, and Helen Stoeckli-Evans. "The crystal structures, Hirshfeld surface analyses and energy frameworks of 8-{1-[3-(cyclopent-1-en-1-yl)benzyl]piperidin-4-yl}-2-methoxyquinoline and 8-{4-[3-(cyclopent-1-en-1-yl)benzyl]piperazin-1-yl}-2-methoxyquinoline." Acta Crystallographica Section E Crystallographic Communications 77, no. 4 (2021): 372–77. http://dx.doi.org/10.1107/s2056989021002474.

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The title compounds, 8-{1-[3-(cyclopent-1-en-1-yl)benzyl]piperidin-4-yl}-2-methoxyquinoline, C27H30N2O (I), and 8-{4-[3-(cyclopent-1-en-1-yl)benzyl]piperazin-1-yl}-2-methoxyquinoline, C26H29N3O (II), differ only in the nature of the central six-membered ring: piperidine in I and piperazine in II. They are isoelectronic (CH cf. N) and isotypic; they both crystallize in the triclinic space group P\overline{1} with very similar unit-cell parameters. Both molecules have a curved shape and very similar conformations. In the biaryl group, the phenyl ring is inclined to the cyclopentene mean plane (r

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31

Prathebha, K., D. Reuben Jonathan, Sathya Shanmugam, and G. Usha. "N-[(1-Benzoylpiperidin-4-yl)methyl]benzamide." Acta Crystallographica Section E Structure Reports Online 70, no. 7 (2014): o771. http://dx.doi.org/10.1107/s1600536814012793.

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In the title compound, C20H22N2O2, the piperidine ring adopts a chair conformation. The phenyl rings are inclined to one another by 80.1 (1)° and make dihedral angles of 46.1 (1) and 40.2 (1)° with the mean plane of the piperidine ring. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into inversion dimers. C—H...O interactions further link the molecules, forming a three-dimensional supramolecular network.

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32

Suresh, J., R. Vishnupriya, S. Sivakumar, R. Ranjith Kumar, and S. Athimoolam. "Intermolecular C—H...O and C—H...Xinteractions in substituted spiroacenaphthylene structures." Acta Crystallographica Section C Crystal Structure Communications 68, no. 7 (2012): o257—o261. http://dx.doi.org/10.1107/s0108270112024584.

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In the three spiroacenaphthylene structures 5′′-[(E)-2,3-dichlorobenzylidene]-7′-(2,3-dichlorophenyl)-1′′-methyldispiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole-6′,3′′-piperidine]-2,4′′-dione, C35H26Cl4N2O2S, (I), 5′′-[(E)-4-fluorobenzylidene]-7′-(4-fluorophenyl)-1′′-methyldispiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole-6′,3′′-piperidine]-2,4′′-dione, C35H28F2N2O2S, (II), and 5′′-[(E)-4-bromobenzylidene]-7′-(4-bromophenyl)-1′′-methyldispiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole-6′,3′′-piperidine]-2,4′′-dione, C35H28Br2N2O2S, (III), the substituted aryl groups are 2,3-d

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33

Sośnicki, Jacek G., and Tomasz J. Idzik. "Pyridones – Powerful Precursors for the Synthesis of Alkaloids, Their Derivatives, and Alkaloid-Inspired Compounds." Synthesis 51, no. 18 (2019): 3369–96. http://dx.doi.org/10.1055/s-0037-1611844.

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2-Pyridone is characterized by a very wide range of reactivity of a different nature, ranging from electrophilic aromatic substitution, CH–metal-mediated reactions, and NH/OH functionalization of both possible lactam/lactim tautomers, through cycloaddition, to nucleophilic addition and transformation of the tautomeric C=O/C–OH moiety. The high availability of 2-pyridones and the possibility of their far-reaching functionalization additionally increased their values. Therefore, they are very useful building blocks for the synthesis of structurally diverse piperidine and pyridine compounds, incl

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34

Farag, I. S. Ahmed, Adel S. Girgis, A. A. Ramadan, A. M. Moustafa, and Ahmed F. Mabied. "5-Chloro-5′′-(4-chlorobenzylidene)-4′-(4-chlorophenyl)-1′,1′′-dimethyldispiro[indoline-3,2′-pyrrolidine-3′,3′′-piperidine]-2,4′′-dione." Acta Crystallographica Section E Structure Reports Online 70, no. 3 (2014): o379—o380. http://dx.doi.org/10.1107/s1600536814004309.

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The racemic title compound, C30H26Cl3N3O2, comprises two spiro links, the first connecting the piperidine and pyrrolidine rings and the other connecting the indole and pyrrolidine rings. The piperidine ring adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation with the unsubstituted C atom as the flap. The dihedral angles between the twop-Cl-substituted benzene rings and the indole ring are 33.13 (14) and 54.11 (14)°. In the crystal, molecules form inversion dimers through pairs of N—H...O hydrogen bonds [graph setR22(8)]. Aromatic C—H...O hydrogen bonds ext

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35

Kia, Yalda, Hasnah Osman, Vikneswaran Murugaiyah, Suhana Arshad, and Ibrahim Abdul Razak. "(3E,5E)-3,5-Bis(4-methylbenzylidene)-1-[3-(piperidin-1-yl)propanoyl]piperidin-4-one." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (2012): o2493—o2494. http://dx.doi.org/10.1107/s1600536812031820.

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In the title compound, C29H34N2O2, the central piperidine ring adopts a half-chair conformation, whereas the terminal one adopts a chair conformation. The mean plane of the central piperidine ring [maximum deviation = 0.384 (2) Å] makes dihedral angles of 64.82 (13) and 17.55 (13)° with the benzene rings. In the crystal, molecules are linked into a tape along thebaxisviaC—H...O interactions, generatingR22(20) andR21(6) graph-set motifs. C—H...π interactions are observed between the tapes.

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36

Baudoin-Dehoux, Cécile, Tessa Castellan, Frédéric Rodriguez, et al. "Selective Targeting of the Interconversion between Glucosylceramide and Ceramide by Scaffold Tailoring of Iminosugar Inhibitors." Molecules 24, no. 2 (2019): 354. http://dx.doi.org/10.3390/molecules24020354.

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A series of simple C-alkyl pyrrolidines already known as cytotoxic inhibitors of ceramide glucosylation in melanoma cells can be converted into their corresponding 6-membered analogues by means of a simple ring expansion. This study illustrated how an isomerisation from iminosugar pyrrolidine toward piperidine could invert their targeting from glucosylceramide (GlcCer) formation toward GlcCer hydrolysis. Thus, we found that the 5-membered ring derivatives did not inhibit the hydrolysis reaction of GlcCer catalysed by lysosomal β-glucocerebrosidase (GBA). On the other hand, the ring-expanded C-

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37

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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38

Trigui, M., S. Pulvin, P. Poupin, and D. Thomas. "Biodegradation of cyclic amines by aPseudomonasstrain involves an amine mono-oxygenase." Canadian Journal of Microbiology 49, no. 3 (2003): 181–88. http://dx.doi.org/10.1139/w03-025.

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Pseudomonas putida O1G3 catalyzes the degradation of pyrrolidine and piperidine. This strain can use these compounds as the sole source of carbon, nitrogen, and energy. When the cyclic amines were used as the growth substrates, the synthesis of a soluble heme amine mono-oxygenase was induced in this bacteria. This observation was confirmed by spectrophotometric analysis and specific inhibitor. This mono-oxygenase is a NADH-dependent enzyme and catalyzes the cleavage of the CN bond of the pyrrolidine and piperidine ring by a mechanism similar to a N dealkylation. This reaction could be followe

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39

Zamoner, Luís O. B., Valquiria Aragão-Leoneti, and Ivone Carvalho. "Iminosugars: Effects of Stereochemistry, Ring Size, and N-Substituents on Glucosidase Activities." Pharmaceuticals 12, no. 3 (2019): 108. http://dx.doi.org/10.3390/ph12030108.

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N-substituted iminosugar analogues are potent inhibitors of glucosidases and glycosyltransferases with broad therapeutic applications, such as treatment of diabetes and Gaucher disease, immunosuppressive activities, and antibacterial and antiviral effects against HIV, HPV, hepatitis C, bovine diarrhea (BVDV), Ebola (EBOV) and Marburg viruses (MARV), influenza, Zika, and dengue virus. Based on our previous work on functionalized isomeric 1,5-dideoxy-1,5-imino-D-gulitol (L-gulo-piperidines, with inverted configuration at C-2 and C-5 in respect to glucose or deoxynojirimycin (DNJ)) and 1,6-dideox

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40

James, Bruce D., Siti Mutrofin, Brian W. Skelton, and Allan H. White. "4-(Piperidin-1-yl)pyridinium hexafluorophosphate at 150 K." Acta Crystallographica Section C Crystal Structure Communications 59, no. 11 (2003): o622—o624. http://dx.doi.org/10.1107/s0108270103019358.

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Structural characterization of the title compound, C10H15N2 +·PF6 −, shows it to be ionic, with the pyridine rather than the piperidine N atom being protonated and forming hydrogen bonds to the counter-ions, resulting in two independent ion pairs. A number of unusual features are noted, in particular the remarkably close inter-ring hydrogen contacts [1.97 (3)–2.00 (3) Å] and the considerable differences in the pair of cations, in respect of the torsion angles within the piperidine ring involving the bonds to either side of the N atom.

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41

Atioğlu, Zeliha, Mehmet Akkurt, Flavien A. A. Toze, Pavel V. Dorovatovskii, Narmina A. Guliyeva, and Humay M. Panahova. "Crystal structure and Hirshfeld surface analysis of dimethyl (3aS,6R,6aS,7S)-2-(2,2,2-trifluoroacetyl)-2,3-dihydro-1H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isoquinoline-3a1,6a-dicarboxylate." Acta Crystallographica Section E Crystallographic Communications 74, no. 11 (2018): 1599–604. http://dx.doi.org/10.1107/s2056989018014305.

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The title molecule, C18H16F3NO7, comprises a fused cyclic system containing four five-membered (two dihydrofuran and two tetrahydrofuran) rings and one six-membered (piperidine) ring. The five-membered dihydrofuran and tetrahydrofuran rings adopt envelope conformations, and the six-membered piperidine ring adopts a distorted chair conformation. Intramolecular O...F interactions help to stabilize the conformational arrangement. In the crystal structure, molecules are linked by weak C—H...O and C—H...F hydrogen bonds, forming a three-dimensional network. The Hirshfeld surface analysis confirms t

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42

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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43

Petrosyan, Artyom V., Astghik A. Shahkhatuni, Andranik M. Davinyan, et al. "Thiol-Epoxy Click Chemistry: The Synthesis of Vicinal Amino Alcohols Containing a 1,2,4-Triazole Ring." Chemistry 7, no. 2 (2025): 53. https://doi.org/10.3390/chemistry7020053.

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As examples of “Click Chemistry”, the reaction of 1-(oxiran-2-ylmethyl)piperidine with several 1,2,4-triazoles derivatives was studied. As a result, the reaction shows that the oxirane ring opens regiospecifically, according to Krasusky’s rule, without using a catalyst. The basic nitrogen present in 1-(oxiran-2-ylmethyl)piperidine has a catalytic (anchimer) effect.

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44

Wang, Xiao-Ling. "8-Oxocanadine." Acta Crystallographica Section E Structure Reports Online 62, no. 5 (2006): o1764—o1765. http://dx.doi.org/10.1107/s1600536806010324.

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The title compound, C20H19NO5, a protoberberine-type alkaloid, was isolated from the roots of the plant Sinomenium acutum. The piperidine ring adopts a screw-boat conformation and the pyridinone ring is in an envelope conformation.

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45

Revathi, B. K., D. Reuben Jonathan, S. Sathya, K. Prathebha, and G. Usha. "Crystal structure of 4-methyl-N-[2-(piperidin-1-yl)ethyl]benzamide monohydrate." Acta Crystallographica Section E Crystallographic Communications 71, no. 5 (2015): o359—o360. http://dx.doi.org/10.1107/s2056989015007653.

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In the title compound, C15H22N2O·H2O, the dihedral angle between the planes of the piperidine and benzene rings is 31.63 (1)°. The piperidine ring adopts a chair conformation. The water solvent molecule is involved in interspecies O—H...O, O—H...N, N—H...O and weak C—H...O hydrogen-bonding interactions, giving rise to chains extending along [010].

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46

Thiruvalluvar, A., and D. Natarajan. "4-Hydroxyimino-2-phenylperhydroquinolinium chloride hemihydrate." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (2007): o4431. http://dx.doi.org/10.1107/s1600536807052245.

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The title compound, C15H21N2O+·Cl−·0.5H2O, crystallizes with two cations, two anions and one water molecule in the asymmetric unit. Both the piperidine and cyclohexane rings adopt chair conformations and the oxime groups are basically planar. The cyclohexane ring is equatorially oriented with respect to the piperidine ring. The crystal structure is stabilized by N—H...Cl, C—H...Cl, C—H...O, N—H...N and O—H...Cl hydrogen bonds. A water molecule that bridges the two crystallographically independent chloride anions via hydrogen bonds is disordered over two chemically equivalent sites, with occupa

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47

Periyannan, P., M. Beemarao, K. Karthik, S. Ponnuswamy, and K. Ravichandran. "Crystal structure, Hirshfeld surface analysis and DFT studies of 1-[r-2,c-6-diphenyl-t-3-(propan-2-yl)piperidin-1-yl]ethan-1-one." Acta Crystallographica Section E Crystallographic Communications 76, no. 3 (2020): 377–81. http://dx.doi.org/10.1107/s2056989020002042.

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In the title compound, C22H27NO, the piperidine ring adopts a chair conformation. The dihedral angles between the mean plane of the piperidine ring and the phenyl rings are 89.78 (7) and 48.30 (8)°. In the crystal, molecules are linked into chains along the b-axis direction by C—H...O hydrogen bonds. The DFT/B3LYP/6–311 G(d,p) method was used to determine the HOMO–LUMO energy levels. The molecular electrostatic potential surfaces were investigated by Hirshfeld surface analysis and two-dimensional fingerprint plots were used to analyse the intermolecular interactions in the molecule.

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48

Tiouabi, Mustapha, Raphaël Tabacchi, and Helen Stoeckli-Evans. "The crystal structure and Hirshfeld surface analysis of 1-(2,5-dimethoxyphenyl)-2,2,6,6-tetramethylpiperidine." Acta Crystallographica Section E Crystallographic Communications 76, no. 6 (2020): 794–97. http://dx.doi.org/10.1107/s2056989020005952.

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In the title compound, C17H27NO2, the piperidine ring has a chair conformation and is positioned normal to the benzene ring. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming chains propagating along the c-axis direction.

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49

Domino, Edward F. "Dr. Paul: Views Through the Piperidine Ring." Anesthesia & Analgesia 107, no. 2 (2008): 723–24. http://dx.doi.org/10.1213/ane.0b013e31817c737d.

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50

Stanley, Theodore H. "Dr. Paul: Views Through the Piperidine Ring." Anesthesia & Analgesia 107, no. 2 (2008): 724. http://dx.doi.org/10.1213/ane.0b013e31817c73a3.

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