1-苄基-4-乙炔基哌啶

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl triphenylphosphonium bromide (25 g) was suspended in tetrahydrofuran (100 ml), followed by the addition of 60% sodium hydride (2.68 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction solution was ice-cooled again, followed by the addition of 1-benzyl-4-piperidone (11.55 g), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a colorless oil (6.08 g, yield; 52%). cooling cooled again the resulting mixture was stirred at room temperature overnight The reaction mixture was partitioned between ethyl acetate and water The resulting organic layer was washed with water dried (over MgSO4) evaporated The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1.19 g of 1-benzyl-4-ethynylpiperidine was dissolved in 20 ml of N,N-dimethylformamide, 1.774 g of (2-cyclohexylmethyloxy)bromobenzene, 114 mg of cuprous iodide, 0.92 ml of triethylamine and 347 mg of tetrakis(triphenylphosphine)palladium were added thereto, and the mixture was stirred at 100° C. for 3.5 hours under anitrogen atmosphere. Ice-water and a diluted ammonia were added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. After filtering through alumina and silica gel, the solvent was evaporated, and the crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to give 316 mg of the title compound as a slight yellow oil. the mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried over anhydrous magnesium sulfate After filtering through alumina and silica gel the solvent was evaporated the crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl triphenylphosphonium bromide (25 g) was suspended in tetrahydrofuran (100 ml), followed by the addition of 60% sodium hydride (2.68 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction solution was ice-cooled again, followed by the addition of 1-benzyl-4-piperidone (11.55 g), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a colorless oil (6.08 g, yield, 52%). cooling cooled again the resulting mixture was stirred at room temperature overnight The reaction mixture was partitioned between ethyl acetate and water The resulting organic layer was washed with water dried (over MgSO4) evaporated The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl triphenylphosphonium bromide (25 g) was suspended in tetrahydrofuran (100 ml), followed by the addition of 60% sodium hydride (2.68 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction solution was ice-cooled again, followed by the addition of 1-benzyl-4-piperidone (11.55 g), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a colorless oil (6.08 g, yield; 52%). cooling cooled again the resulting mixture was stirred at room temperature overnight The reaction mixture was partitioned between ethyl acetate and water The resulting organic layer was washed with water dried (over MgSO4) evaporated The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)