Ammonia → HCID 22678514, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence