4-Chloroaniline → Tert-butyl 4-(4-chlorophenylamino)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl-4-oxopiperidine-1-carboxylate (1.0 g, 0.005 mmol) in tetrahydrofuran (16 mL) in a microwave reaction vessel were added 4-chloroaniline (640 mg, 0.005 mmol) and sodium triacetoxyboryhidride (3.2 g, 0.015 mmol), followed by irradiating the solution with microwaves at 80° C. for 10 min. The reaction was terminated by the addition of distilled water. The resulting reaction mixture was diluted in ethyl acetate (100 mL) and washed with distilled water (200 mL) to separate an organic solvent layer. The organic solvent layer was dried over anhydrous magnesium sulfate and evaporated at reduced pressure. Isolation and purification of the residue through silica gel chromatography produced tert-butyl-4-(4-chlorophenylamino)piperidine-1-carboxylate (yield: 65%).

Provenance & Evidence