Hydrogen Bromide → 1-(4-bromophenyl)-N,N-dimethylpiperidine-4-carboxamide

Participants

Reaction Steps

A solution of 1-(4-aminophenyl)-N,N-dimethylpiperidine-4-carboxamide (4.2 g, 16.98 mmol) in 25 mL HBr in 20 mL of water was added a solution of NaNO2 (1.17 g, 16.98 mmol) in water (2 mL) slowly. The mixture was stirred at −10° C.˜0° C. for 30 minutes, and added dropwise to a solution of CuBr (1.34 g, 9.34 mmol) in 12 mL HBr in water (10 mL). Then the mixture was stirred at reflux for 2 hours. The mixture was partitioned between 2N NaOH and EA, washed with EA, dried over Na2SO4. The volatiles were removed in vacuo, and the residue was purified by chromatography with PE/EA (15:1˜2:1) to give 2.5 g of 1-(4-bromophenyl)-N,N-dimethylpiperidine-4-carboxamide.

Provenance & Evidence