Hydrochloric Acid → 3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide hydrochloride

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Reaction Steps

As described for Example 120, 650 mg of a cis-trans mixture of N,N-dimethyl-1-phenlcyclohexane-1,4-diamine were reacted with 810 mg 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylic acid (1 molar equivalent) and the crude product (1.92 g) was isolated. The main fraction, obtained after column chromatography on silica gel (3.0×19 cm) with 175 ml diethyl ether followed by 250 ml diethyl ether/methanol (V:V=2:1), 250 ml diethyl ether/methanol (V:V=1:1) and 100 ml methanol, of 1.10 g was dissolved in 15 ml 2-butanone and 15 ml ethyl acetate and converted into the corresponding hydrochloride of the non-polar diastereoisomer of 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide by adding 42 μl water, 296 μl chlorotrimethylsilane and 25 ml diisopropylether (311 mg of white solid).

Provenance & Evidence