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Synthesis and spectral analysis of (±)‐ cis ‐ N ‐[1‐(2‐hydroxy‐2‐phenyl‐ethyl)‐3‐methyl‐4‐piperidyl]‐ N ‐phenylpropanamide and (±)‐ cis ‐ N ‐[1‐(2‐hydroxy‐1‐phenylethyl)‐3‐methyl‐4‐piperidyl]‐ N ‐phenylpropanamide
Author(s) -
Brine G. A.,
Sawyer D. K.,
Huang P.T.,
Stark P. A.,
Gaetano K. D.,
Carroll F. I.
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290717
Subject(s) - chemistry , heteronuclear molecule , stereochemistry , styrene , medicinal chemistry , nuclear magnetic resonance spectroscopy , organic chemistry , copolymer , polymer
Treatment of (±)‐ cis‐N ‐(3‐methyl‐4‐piperidyl)‐ N ‐phenylpropanamide (2) with styrene oxide (1) yielded a mixture of (±)‐ cis ‐ N ‐[1‐(2‐hydroxy‐2‐phenylethyl)‐3‐methyl‐4‐piperidyl]‐ N ‐phenylpropanamide (3) and (±)‐ cis ‐ N ‐[1‐(2‐hydroxy‐1‐phenylethyl)‐3‐methyl‐4‐piperidyl]‐ N ‐phenylpropanamide (4) . The structure of compound 3 was confirmed by an unambiguous synthesis via (±)‐ cis ‐ N ‐[1‐(2‐oxo‐2‐phenylethyl)‐3‐methyl‐4‐piperidyl]‐ N ‐phenylpropanamide (6) . The proton and carbon‐13 resonances of compounds 3 and 4 were assigned with the aid of two‐dimensional heteronuclear correlation experiments.