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 | Zendy

Brine G. A. | Zendy; Sawyer D. K. | Zendy; Huang P.T. | Zendy; Stark P. A. | Zendy; Gaetano K. D. | Zendy; Carroll F. I. | Zendy

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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.

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