The Preparation of Some Piperidine Derivatives by the Mannich Reaction

Noller, C. R.; Baliah, V.

doi:10.1021/ja01191a092

Cited by 246 publications

(109 citation statements)

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“…The deshielding magnitude observed on H(2) in the Z isomers (syn α protons) are roughly same as those observed on H (6) in the E isomers (syn α protons) and the magnitude of deshielding is ≈ 2 ppm in 1-4. The deshielding magnitude of syn α protons higher than the syn α axial protons.…”

Section: Analysis Of Chemical Shiftssupporting

confidence: 69%

“…The NOESY and 1 H-13 C COSY spectra were recorded on a Bruker DRX 500 NMR spectrophotometer. The starting compound t(3)-ethyl-r(2),c(6)-di(2'-furyl)piperidin-4-one was prepared by the general procedure reported by Noller and Baliah 6 . A mixture of ammonium acetate (0.05 mol), furfuraldehyde (0.1 mol) and pentan-2-one (0.05 mol) in distilled ethanol was heated first to boiling and then stirred under the cold condition for 1 hr.…”

Section: Methodsmentioning

confidence: 99%

“…Mannich reaction is one of the multicomponent reactions for the carbon-carbon and carbon-hetero atom sequential bond formation. Mannich type condensation involving aromatic aldehydes, ammonium acetate and ketones having two active methylene groups, resulting in the formation of 2,6-diarylpiperidin-4-ones, was first reported by Noller and Baliah 6 . In the course of developing biologically active molecules, we have recently reported the synthesis and conformational studies of N-acyl-t(3)-methyl -2,6-difurylpiperidin-4-ones 7 and N-acyl-t(3)-isopropyl-2,6-difurylpiperidin-4-one oxime derivatives 8 .…”

Section: Introductionmentioning

confidence: 96%

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Synthesis and Spectral Characterization of Some Novel N-Acyl-Piperidin-4-Ones

Selvaraju¹,

Manimekalai²

2017

Rasayan J. Chem.

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A collection of novel N-acyl-t(3)-ethyl-r(2),c(6)-di(2'-furyl)piperidin-4-ones 1-4 are synthesized, characterized by melting point, one-dimensional NMR ( 1 H and 13 C) and two-dimensional NOESY and 1 H-13 C COSY spectrum. The spectra reveal the presence of two isomeric forms i.e., E and Z isomers for 1-4. The effect of varying the substituents at nitrogen on the 1 H and 13 C chemical shifts have been analyzed in detail.

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Section: Analysis Of Chemical Shiftssupporting

confidence: 69%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

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Synthesis and Spectral Characterization of Some Novel N-Acyl-Piperidin-4-Ones

Selvaraju¹,

Manimekalai²

2017

Rasayan J. Chem.

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“…The synthesis of 2, 6-bis(4-fluorophenyl)-3,5-dimethylpiperidin-4-one was carried out by following the procedure available in the literature [27]. A mixture of diethylketone (0.86 g, 0.01 mole), fluorobenzaldehyde (2.48 g, 0.02 mole) and ammonium acetate (0.85g, 0.011 mole) in methanol was refluxed for about 0.5 h. The reaction mixture was then cooled to room temperature.…”

Section: Synthesis and Crystal Growthmentioning

confidence: 99%

Hydrogen bonding in 2,6-bis(4-fluorophenyl)-3,5-dimethylpiperidin-4-one methanol solvate

Suresh¹,

Vijayakumar

Kumar

et al. 2016

Zeitschrift Für Kristallographie - Crystalline Materials

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Hydrogen bonding in 2,6-bis(4-fluorophenyl)-3,5-dimethylpiperidin-4-one methanol solvate 72S.docx 30.10.2017 1 (21) Hydrogen bonding in a piperidin-4-one Keywords: Piperidin-4-one / conformation / DFT / crystal structure analysis / X-ray diffraction Abstract. The crystal structure analysis of a 2,6-diaryl 4-piperidone derivative, isolated as a mono-methanol solvate, reveals that both the piperidone and the methanol molecule lie on a crystallographic mirror plane. A chair conformation is found for the piperidone ring with the aryl and methyl groups in equatorial positions. The most prominent feature of the molecular packing is the formation of supramolecular zigzag chains mediated by amine-N-H…O(methanol) and hydroxyl-O-H…N(amine) hydrogen bonds, i.e. the methanol molecule serves as a bridge between piperidone molecules. The molecular structure is compared with that determined in an unsolvated form and the gas-phase equilibrium structure, obtained using density-functional theory (DFT); differences relate, in the main, to the relative dispositions of the aryl rings. An analysis of the Hirshfeld surfaces of the experimental structures indicates very similar relative contributions with the notable exception being the contribution by O…H/H…O which at 13.7% in the methanol solvate is greater than 8.5% in the unsolvated form.

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“…3-Methyl-2,6-diphenylpiperidin-4-one 1 (1.32 g, 0.005 mol), prepared according to the reported literature [7] and formaldehyde (3 mL) were dissolved in a mixture of ethanol (25 mL) and DMF (10 mL). The contents were warmed on a water bath maintained at 60 °C and morpholine (1 mL, 0.01 mol) was added with constant stirring.…”

Section: Preparation Of 3-methyl-1-morpholin-4-ylmethyl-2 6-diphenylmentioning

confidence: 99%