Phthalimide → N-[2-[1-(4-fluorobenzyl)piperidin-4-yl]ethyl]phthalimide

Participants

Reaction Steps

To a mixture of 1-(4-fluorobenzyl)-4-(2-hydroxyethyl)piperidine (10.0 g), triphenylphosphine (13.04 g) and phthalimide (6.65 g) in tetrahydrofuran (100 ml) was added dropwise a solution of diethyl diazenedicarboxylate (7.7 ml) in tetrahydrofuran (50 ml). After stirring overnight at ambient temperature, the mixture was evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with water and brine, and dried over magnesium sulfate, and evaporated in vacuo. The residue was suspended with hexane--ether (100 ml--100 ml) and the precipitates were removed by filtration. The filtrate was evaporated in vacuo and the residue was recrystallized from hexane to give N-[2-[1-(4-fluorobenzyl)piperidin4-yl]ethyl]phthalimide (9.23 g).

Provenance & Evidence