Benzonitrile, 4-bromo- → 1-Boc-4-[(4-cyanophenyl)amino]-piperidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (Willoughby, Christopher A.; Bioorg. Med. Chem. Lett., 13, 3, 2003, 427-432) (311 mg, 1.55 mmol), 4-bromobenzonitrile (237 mg, 1.30 mmol), Pd2(dba)3 (21 mg, 0.023 mmol), (±)-BINAP (48 mg, 0.077 mmol) and t-BuONa (136 mg, 1.42 mmol) in freshly degassed toluene (4.5 mL) was stirred at 85° C. under argon for 2 hours. Work-up and purification gave 4-(4-cyano-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester as an orange solid (324 mg, 83%).

Provenance & Evidence