Hydrochloric Acid → 1-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

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Reaction Steps

By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (5 g), phosphorus oxychloride (2.47 cc), 4-bromothiophenol (5.39 g) and sodium cyanoborohydride (1 g), a chestnut-coloured residue is obtained which is taken up in chloroform. The solution is made alkaline to pH 10 with an aqueous solution of sodium hydroxide. After separation of the chloroform phase, the aqueous phase is extracted with methylene chloride. The organic phases are collected, dried over sodium sulphate, filtered and then evaporated to dryness under reduced pressure (2.7 kPa) at 30° C. A residue is obtained which is dissolved in ethanol (60 cc). A 3N ether solution (7.7 cc) of hydrochloric acid gas is added to this solution. The white solid which precipitates is separated off by filtration and recrystallised from a mixture of isopropanol and methanol (60/40 by volume). In this way 3-(4-bromophenylthio)-1-dimethylamino-3-phenyl-2-propene (Z) hydrochloride (1.8 g) is obtained in the form of a white solid melting at 252° C.

Provenance & Evidence