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The base‐catalyzed alkylation of rac.‐trans‐tetrahydro‐6‐hydroxy‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(2H)‐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(2H)‐one (2) and in addition, 2,3‐dihydro‐4‐[2‐(dimethylamino)‐ethyl]‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(4H)‐one (3). A plausible mechanism is postulated for the dehydration of the rac.‐trans‐amide 2.
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Mohacsi et al. (1991) studied this question.
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