Hydrochloric Acid → HCID 68892678, compound

Participants

Reaction Steps

As described for Example 61, 310 mg 3-(4-chlorobenzoyl) propanoic acid dissolved in 1.6 ml DMF were added to 350 mg of the polar diastereoisomer of N,N-dimethyl-1-phenylcyclohexane-1,4-diamine, 230 [L N,N-diisopropylcarbodiimide and 200 μg 1-hydroxybenzotriazole (HOBt) at 0° C. and while stirring. After three hours at this temperature, the mixture was stirred overnight while heating to room temperature. For working up, one-molar sodium carbonate solution was added (pH>10) and the crude product (1.193 mg) was isolated by extraction with ethylacetate/THF (V:V=1:1), subsequent drying over sodium sulphate and evaporation. The main fraction of 413 mg obtained by column chromatography on silica gel (4.0×18 cm) with methanol/ethylacetate/n-hexane (V:V:V=1:1:1) was dissolved in 41 ml ethylacetate and was converted into the corresponding hydrochloride of the polar diastereoisomer of 4-(4-chloro-phenyl)-N-(4-dimethylamino-4-phenylcyclohexyl)-4-oxobutyramide by adding 18 μl water and 130 μl chlorotrimethylsilane (321 mg white solid).

Provenance & Evidence