Triethylamine → Benzyl 4-aminobenzylcarbamate

Participants

Reaction Steps

To a solution of 4-aminobenzenemethanamine (1.5 g, 12.3 mmol) in 20 mL CH2Cl2 was added benzylchloroformate (1.57 mL, 11 mmol), followed by triethylamine (Et3N) (1.5 mL, 11 mmol) at room temperature. White percipitates was observed immediately. The reaction was stirred at room temperature for 10 minutes and removed Et3N salt by filtration. The reaction mixture was concentrated in vacuo and partitioned between EtOAc and H2O. The EtOAc layer was washed with a sat. solution of KHSO4, a sat. solution of NaHCO3, concentrated in vacuo and subjected to a silica-gel column using CHCl3 /CH3 OH=25/1 ratio as an eluting solvent to give title compound (43% yield).

Provenance & Evidence