Hydrochloric Acid → HCID 86612018, compound

Participants

Reaction Steps

280 mg 4-benzoylbutyric acid (5-oxo-5-phenyl pentanoic acid) dissolved in 1.4 ml DMF were added to 350 mg of the non-polar diastereoisomer of N,N-dimethyl-1-phenylcyclohexane-1,4-diamine, 230 μl N,N-diisopropylcarbodiimide and 200 μg 1-hydroxybenzotriazole (HOBt) at about 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 (674 mg) isolated by extraction with ethylacetate, subsequent drying over sodium sulphate and evaporation. The main fraction of 295 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 135 ml ethylacetate and was converted into the corresponding hydrochloride of the non-polar diastereoisomer of 5-oxo-5-phenyl pentanoic acid (4-dimethylamino-4-phenylcyclohexyl)amide by adding 12 μl water and 90 μl chlorotrimethylsilane (310 mg white solid, mp. 127-137° C.).

Provenance & Evidence