NDLI: Convenient synthesis and NMR spectral studies of variously substituted N-methylpiperidin-4-one-O-benzyloximes

Content Provider	Springer Nature Link
Author	Parthiban, Paramasivam Rani, Mannangatty Kabilan, Senthamaraikannan
Copyright Year	2008
Abstract	A series of variously substituted N-methylpiperidin-4-one-O-benzyloximes were synthesized by three different methods. Among them, the direct conversion of 2,6-diarylpiperidin-4-ones into the corresponding oxime ethers (method A) was proved to be better than the other two methods in the sense of good yield, convenience, easy work-up and quick reaction time. All the synthesized compounds are characterized by IR, Mass and NMR (1H NMR, 13C NMR, 1H-1H COSY, 1H-13C COSY and HMBC) spectral studies. The conformational preference of the synthesized oxime ethers with/without alkyl and aryl substituents at C-3/C-5 and C-2/C-6 is discussed using the spectral data. The observed chemical shifts and coupling constants suggest that the synthesized oxime ethers adopt chair conformation with equatorial orientation of all the substituents, whereas 1-methyl-3-isopropyl-2,6-diphenylpiperidin-4-one-O-benzyloxime also exists in boat conformation. Based on the NMR data, the effects of oximination on ring carbons and their associated protons and alkyl substituents are discussed. In addition, the effect of NMe group on the 2,6-diarylpiperidin-4-one-O-benzyloximes was also studied.
Starting Page	287
Ending Page	301
Page Count	15
File Format	PDF
ISSN	00269247
Journal	Monatshefte für Chemie - Chemical Monthly
Volume Number	140
Issue Number	3
e-ISSN	14344475
Language	English
Publisher	Springer Vienna
Publisher Date	2008-09-25
Publisher Place	Vienna
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	N-Methylpiperidin-4-ones Oxime ether NMR Effect of oximination Effect of N-methylation Theoretical and Computational Chemistry Physical Chemistry Organic Chemistry Inorganic Chemistry Analytical Chemistry Chemistry/Food Science
Content Type	Text
Resource Type	Article
Subject	Chemistry

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