Acetone → 1-(1-Hydroxy-1,2,3,4-tetrahydro-1-naphthyl)-3-dimethylamino-1-phenyl-1-propene

Participants

Reaction Steps

By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (5 g), phosphorus oxychloride (2.5 cc), 3-chlorothiophenol (4.13 g) and sodium cyanoborohydride (1 g), and after evaporating the organic phase to dryness under reduced pressure (2.7 kPa) at 40° C., a residue is obtained which is dissolved in a mixture (20 cc) of acetone and ethyl ether (50/50 by volume). A 5.6N solution (6 cc) of hydrochloric acid gas in ethyl ether is added to this solution. The precipitate formed is separated off by filtration and then recrystallised from isopropanol (30 cc). In this way 3-(3-chlorophenylthio)-1-dimethylamino-3-phenyl-2-propene (Z) hydrochloride (2.6 g) is obtained in the form of a white solid melting at 156°-157° C.

Provenance & Evidence