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 | Health & Environmental Research Online (HERO)

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Tags

HERO ID

6654832

Reference Type

Journal Article

Title

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

Author(s)

Brine, GA; Sawyer, DK; Huang, PT; Stark, PA; Gaetano, KD; Carroll, FI; ,

Year

1992

Is Peer Reviewed?

Yes

Journal

Journal of Heterocyclic Chemistry
ISSN: 0022-152X

Publisher

WILEY

Location

HOBOKEN

Volume

Issue

Page Numbers

1773-1779

Language

English

DOI

10.1002/jhet.5570290717

Web of Science Id

WOS:A1992KH40900017

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0027097081&doi=10.1002%2fjhet.5570290717&partnerID=40&md5=ae85635677a911aa553d8d8495899868
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Abstract

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.