Hydrochloric Acid → alpha-methyl-N-ethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine

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Reaction Steps

To 5.3 g. (about 8 equivalents) of ethylamine and 10 g. of molecular sieve 3A in 100 ml. absolute methanol are added at 0° C. 5.6 ml. of 5 N methanolic hydrochloric acid (2 equivalents) and then 3 g. of (1-phenyl-2,5-cyclohexadien-1-yl)-2-propanone in a small amount of absolute methanol. 0.63 g. (0.7 equivalent) of sodium cyanoborohydride is then added and the mixture is stirred at room temperature for 5 days. The mixture is worked-up in exactly the same manner as described in Example 16. The crude product is chromatographed on silica gel with methylene chloride/methanol (10:1). There is obtained α-methyl-N-ethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine as an oily product. This product is converted as usual into the hydrochloride which, after crystallization from methylene chloride/ether, has a melting point of 151°-153° C.

Provenance & Evidence