Synthesis and NMR study of the stereochemistry of r(2),c(6)-diaryl-c(3)-chloropiperidin-4-ones

r(2),c(6)-Diaryl-c(3)-chloropiperidin-4-ones have been obtained by the epimerization of r(2),c(6)-diaryl-t(3)chloropiperidin-4-ones by treatment with ammonia in DMF. The H-1 and C-13 NMR spectra of these piperidones were measured in CDCl3 at 360 and 90 MHz respectively and the chemical shifts assign...

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Published inIndian journal of chemistry. Sect. B. Organic chemistry, including medicinal chemistry Vol. 43; no. 10; pp. 2147 - 2151
Main Authors Perumal, S, Manonmani, Vijayabaskar, Selvaraj, S, Lycka, A
Format Journal Article
LanguageEnglish
Published NEW DELHI Natl Inst Science Communication & Information Resources-Niscair 01.10.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:r(2),c(6)-Diaryl-c(3)-chloropiperidin-4-ones have been obtained by the epimerization of r(2),c(6)-diaryl-t(3)chloropiperidin-4-ones by treatment with ammonia in DMF. The H-1 and C-13 NMR spectra of these piperidones were measured in CDCl3 at 360 and 90 MHz respectively and the chemical shifts assigned unambiguously employing one dimensional H-1 and C-13 and two-dimensional H,H-COSY, C,H-COSY and NOESY NMR spectra. NMR spectroscopic parameters of the epimeric pair of chloropiperidones have been compared and the differences rationalized in terms of stereochemical features.
ISSN:0376-4699
0019-5103