Hydrochloric Acid → 5-Methyl-3-phenylisoxazole-4-carboxylic acid [4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]amide hydrochloride

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Reaction Steps

As described for Example 120, 700 mg of a cis-trans mixture of 1-(3-fluorophenyl)-N,N-dimethylcyclohexane-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 (3.0×19 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 200 ml methanol, of 775 mg was dissolved in 10 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-(3-fluorophenyl)cyclohexyl]amide by adding 33 μl water and 233 μl chlorotrimethylsilane (423 mg of white solid, Mp. 256-259° C.).

Provenance & Evidence