Benzhydrol → 4-Benzhydryloxypiperidine

Participants

Reaction Steps

Molecular sieves, benzhydrol (1.1 g, 5.5 mmol), and p-toluenesulfonic acid monohydrate (1.0 g, 5.5 mmol) were added to a suspension of 4-hydroxypiperidine (505 mg, 5 mmol) in toluene, and the mixture was refluxed for 3 hours while removing water using a Dean-Stark condenser. After the completion of the reaction was confirmed by HPLC, the reaction mixture was allowed to cool down to a room temperature. From the reaction mixture, the insoluble matter was removed, and then the solvent was distilled off. The resulting residue was dissolved in ethyl acetate and washed with a 2-N sodium hydroxide solution 3 times. The organic layer was dried over magnesium sulfate, and then the solvent was distilled off. Thus the title compound (676 mg, 50.6%) was obtained as an oily substance.

Provenance & Evidence