4-Isoxazolecarbonyl chloride, 3-(2-chlorophenyl)-5-methyl- → 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid [4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]amide

Beteiligte Stoffe

Reaktionsschritte

As described for Example 118, the polar diastereoisomer of 1-(3-fluorophenyl)-N,N-dimethylcyclohexane-1,4-diamine (350 mg) was reacted with 400 mg 3-(2-chlorophenyl)-5-methylisoxazole-4-carbonylchloride and worked up in a similar manner. The resultant crude product (590 mg) was chromatographed on silica gel (4.0×15 cm) with ethyl acetate/n-hexane/methanol (V:V=1:1:1). 440 mg of the polar diastereoisomer of 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxylic acid [4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]amide were obtained which, dissolved in 90 ml 2-butanone, were converted overnight into the corresponding hydrochloride by adding 17 μl water and 120 μl chlorotrimethylsilane (460 mg of white solid, Mp. 209-211° C.).

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