(+-)-Methionine → 8-hydroxy-7-methoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine

Participants

Reaction Steps

A mixture of 2.6 g. (0.008 mole) of 7,8-dimethoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine (prepared as in Example 3) and 1.26 g. (0.0085 mole) of dl-methionine in 35 ml. of methanesulfonic acid was stirred at room temperature for 3.5 hours. The reaction mixture was quenched with ice/water, made basic with 10% sodium hydroxide solution to pH 8.5 and extracted with chloroform. The extract was washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated to give 2.18 g. (87% yield) of 8-hydroxy-7-methoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 161°-162° C.

Provenance & Evidence