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

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.

1. customthe precipitate was removed by vacuum filtration
2. washThe benzene filtrate was washed with aqueous sodium bicarbonate solution
3. dry with materialwith water, dried
4. customthe benzene evaporated off
5. dissolutionThe residue was dissolved in 300 ml of absolute ethanol
6. customthe solution was reacted with hydrogen at 50° C in the presence of 4.5 g of 5%
7. customwas absorbed
8. filtrationThe catalyst was filtered off
9. customafter evaporation of the ethanol
10. distillationthe residue was distilled

ORD record

ord-d5bb84fe1bbd4b76918219fe1020465d

Source dataset

uspto-grants-1977_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04018922