SYNTHESIS AND SPECTRAL-ANALYSIS OF (+/-)-CIS-N-[1-(2-HYDROXY-2-PHENYLETHYL)-3-METHYL-4-PIPERIDYL]-N-PHENYLPROPANAMIDE AND (+/-)-CIS-N-[1-(2-HYDROXY-1-PHENYLETHYL)-3-METHYL-4-PIPERIDYL]-N-PHENYLPROPANAMIDE

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 s...

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Published inJournal of heterocyclic chemistry Vol. 29; no. 7; pp. 1773 - 1779
Main Authors BRINE, GA, SAWYER, DK, HUANG, PT, STARK, PA, GAETANO, KD, CARROLL, FI
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.12.1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALUMINA SURFACES
MILD
ANALGESICS
FENTANYL ANALOGS
ORGANIC-REACTIONS
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Summary: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.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570290717