Diethyl Ether → 1-(1-Ethynylcyclohexyl)piperidine

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7.0 g of 1-acetoxy-1-ethynylcyclohexane (Production Example 17) was dissolved in 140 ml of tetrahydrofuran, and after 20.8 ml of piperidine was added dropwise thereto at room temperature, 208 mg of copper chloride (I) was added to the resulting yellow transparent solution. The resulting mixture was stirred in an oil bath at 95° C. for 2 hours. The reaction mixture was left to stand to cool to room temperature, 200 ml of diethyl ether was added thereto and extracted with 100 ml of an aqueous 2 N hydrochloric solution twice. After addition of about 200 ml of ice to the resultant acidic solution, sodium hydroxide was added to the solution until the solution became basic (pH=10). The solution was extracted with 100 ml of dichloromethane twice. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed, to give a brown solid. To the solid was added hexane and washed, and the solid was collected by filtration, to give 700 mg of the title compound.

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