Hydrochloric Acid → 1-(4-Butyl-4-dimethylaminocyclohexyl)-2-phenylethanol

Participants

Reaction Steps

2 M hydrochloric acid (20 ml) was added to a solution of {1-butyl-4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexyl}dimethylamine (1.09 g, 2.90 mmol) in anhydrous tetrahydrofuran (20 ml) and the mixture was stirred at room temperature for 3 d. The tetrahydrofuran was removed i. vac. and the acid aqueous solution was extracted with diethyl ether (3×10 ml) and thereafter rendered alkaline with 4 M sodium hydroxide solution. The alkaline phase was extracted with methylene chloride (4×10 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac. The crude product (646 mg) was purified by flash chromatography with methylene chloride/methanol (9:1→8:2→0:1). The product obtained in this way was in the form of the hydrochloride. It was taken up in methylene chloride and the suspension was washed with saturated potassium carbonate solution. The organic phase was dried with sodium sulfate and concentrated i. vac.

Provenance & Evidence