Hydrochloric Acid → HCID 86612018, compound

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Reaction Steps

As described for Example 63, 280 mg 5-oxo-5-phenylpentanoylchloride dissolved in 1.6 ml DMF were added to 350 mg of the polar diastereoisomer of N,N-dimethylamino-1-phenylcyclohexane-1,4-diamine, 230 μl N,N-diisopropylcarbodiimide and 200 μg 1-hydroxybenzotriazole (HOBt) at 5° C. 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 (794 mg) isolated by extraction with ethylacetate, subsequent drying over sodium sulphate and evaporation. The main fraction of 410 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 5-oxo-5-phenylpentanoic acid (4-dimethylamino-4-phenylcyclohexyl)amide by adding 19 μl water and 130 μl chlorotrimethylsilane (322 mg white solid).

Provenance & Evidence