Benzene → Ethyl 2-(4-piperidyloxy)-octanoate

Participants

Reaction Steps

32.4 g (0.2 mole) of octanoyl chloride were added dropwise at 20° C (cooling with an ice bath) to a solution of 47 g (0.2 mole) of 2-(1-benzyl-4-piperidyloxy)-ethanol and 20.2 g (0.2 mole) of triethylamine in 300 ml of benzene and after standing for 24 hours at room temperature, the precipitate was removed by vacuum filtration. The benzene filtrate was washed with aqueous sodium bicarbonate solution, then with water, dried and the benzene evaporated off. The residue was dissolved in 300 ml of absolute ethanol and the solution was reacted with hydrogen at 50° C in the presence of 4.5 g of 5% palladized charcoal until the theoretical amount of hydrogen was absorbed. The catalyst was filtered off and after evaporation of the ethanol, the residue was distilled to obtain 35.5 g (64% yield) of ethyl 2-(4-piperidyloxy)-octanoate as a clear oil boiling at 150°-156° C at 0.1 mm Hg and having a refractive index nd20 = 1.464.

Provenance & Evidence