Phenethylamine → 4-bromo-N-phenylbenzamide

Reaction equation

C(N)C[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](Cl)=[O:18])=[CH:13][CH:12]=1.C([N:22](CC)CC)C>ClCCl>[C:3]1([NH:22][C:17](=[O:18])[C:14]2[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Procedure

Phenethylamine (1.2 mL, 9.57 mmol) was added slowly to a mixture of 4-Bromo-1-benzenecarbonyl chloride (2.0 g, 9.11 mmol) and triethyl amine (1.9 mL, 13.67 mmol) in dichloromethane (95 mL). After 3 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was re-crystallized from ethyl acetate/heptane to give N1-phenyl-4-bromobenzamide (1.925 g, 69%). 1H NMR (DMSO-d6) δ 2.84 (m, 2H), 3.47 (m, 2H), 7.28 (m, 5H), 7.67 (d, J=8.59 Hz, 2H), 7.76 (d, J=8.59 Hz, 4H), 8.64 (m, 1H).