Hydrochloric Acid → 5-Methyl-3-phenylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide hydrochloride

Participants

Reaction Steps

As described for Example 120, 650 mg of a cis-trans mixture of N,N-dimethyl-1-phenylcyclohexane-1,4-diamine were reacted with 600 mg 5-methyl-3-phenylisoxazole-4-carboxylic acid (1 molar equivalent) and the crude product was isolated. The main fraction, obtained after column chromatography on silica gel (3.0×18 cm) with 100 ml diethyl ether followed by 350 ml diethyl ether/methanol (V:V=2:1), of 560 mg was dissolved in 20 ml 2-butanone and 10 ml ethyl acetate and converted into the corresponding hydrochloride of the non-polar diastereoisomer of 5-methyl-3-phenylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide by adding 25 μl water and 176 μl chlorotrimethylsilane (372 mg of white solid, Mp. 220-224° C.).

Provenance & Evidence