Hydrochloric Acid → 1-(4-Dimethylamino-4-thiophen-2-yl-cyclohexyl)-2-phenylethanol

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Reaction Steps

2 M hydrochloric acid (20 ml) was added to a solution of {4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]-1-thiophen-2-yl-cyclohexyl}dimethylamine (1.10 g, 2.73 mmol) in tetrahydrofuran (20 ml) and the reaction mixture was stirred at room temperature overnight. It was then rendered alkaline with 4 M sodium hydroxide solution and extracted with methylene chloride (4×10 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac. The crude product (956 mg) was purified by flash chromatography with cyclohexane/ethyl acetate (3:2) and then methanol. The two product fractions obtained in this way were each taken up in diethyl ether, and 2 M hydrochloric acid (20 ml) was added. The phases were separated. The acid aqueous phases were extracted with diethyl ether (3×10 ml) and thereafter rendered alkaline with 4 M sodium hydroxide solution. The aqueous phases were extracted with methylene chloride (4×10 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac.

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