Acetic Acid → 1-(4-Oxo-4-[4-fluorophenyl]butyl)-3-(3-hydroxyphenyl)piperidine

Participants

Reaction Steps

A mixture of 1.4 g (4 mmole) of 1-(4-oxo-4-[4fluorophenyl]butyl)-3-(3-methoxyphenyl)piperidine, 10 ml of 48% aqueous hydrobromic acid and 5 ml of glacial acetic acid was heated under reflux for ca. 20 hours. The reaction mixture was then poured onto a mixture of ice and water. The resulting mixture was basified with potassium carbonate and then it was extracted with ethyl acetate. The extracts were washed with water, followed by saturated sodium chloride solution, and then they were dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography on 150 ml of silica gel, eluting with chloroform/methanol (95:5). The product was then recrystallized from chloroform to give 540 mg (30% yield) of the title compound as a chloroform solvate, m.p. 77°-78° C.

Provenance & Evidence