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The base‐promoted dehydration of rac.‐ trans ‐tetrahydro‐6‐hydroxy‐4‐[(2‐(dimethylamino)ethyl]‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(2 H )‐one
Author(s) -
Mohacsi Erno,
O'Brien Jay P.
Publication year - 1991
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.5570280845
Subject(s) - chemistry , alkylation , dehydration , dimethyl sulfoxide , base (topology) , amide , medicinal chemistry , stereochemistry , chloride , catalysis , organic chemistry , biochemistry , mathematical analysis , mathematics
Abstract The base‐catalyzed alkylation of rac.‐ trans ‐tetrahydro‐6‐hydroxy‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(2 H )‐one ( 1 ) with dimethylaminoethyl chloride in dimethyl sulfoxide provided predominantly rac.‐ trans ‐tetrahydro‐6‐hydroxy‐4‐[(2‐dimethylamino)ethyl]‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(2 H )‐one ( 2 ) and in addition, 2,3‐dihydro‐4‐[2‐(dimethylamino)‐ethyl]‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(4 H )‐one ( 3 ). A plausible mechanism is postulated for the dehydration of the rac.‐ trans ‐amide 2 .