O-Methyltyramine → HCID 14151504, compound

Participants

Reaction Steps

According to the Procedure A above, 4-methoxyphenethylamine is reacted with styrene oxide and the resulting N-(2-hydroxy-2-phenyl)ethyl-4-methoxyphenethylamine is cyclized with acid to give 8-methoxy1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine. A salt, for example the hydrochloride, of this compound is reacted with bromine to give the 7-bromo compound which is reacted with butyllithium and phenyl disulfide or trifluoromethanesulfenyl chloride to give 8-methoxy-1-phenyl-7-phenylthio(or 7-trifluoromethylthio)-2,3,4,5-tetrahydro-1H-3-benzazepine. The 8-hydroxy compounds are prepared by O-demethylating the 8-methoxy compounds by standard procedures.

Provenance & Evidence