Triethylamine → Benzyl 4-aminophenethylcarbamate

Participants

Reaction Conditions

Reaction Steps

A solution of 5.00 g (36.7 mmol) of 2-(4-aminophenyl)ethylamine in 100 mL of chloroform was cooled to 0° C. and 3.72 g (5.20 mL, 36.8 mmol) of triethylamine was added. A solution of 6.26 g (5.2 mL, 36.8 mmol) of benzyl chloroformate in 40 mL of chloroform was then added dropwise over a 30-min period. The reaction was allowed to stir at 0° C. for 2 h. It was diluted with 100 mL of chloroform, washed with 100-mL portions of water and brine, dried over sodium sulfate and concentrated. The residue was dissolved in 50% ethyl acetate/hexane and stirred with 30 g of silica gel, filtered, and concentrated. Further purification by recrystallization from ethyl acetate/hexanes gave 4.82 g (49%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) 7.33 (s, 5H), 6.94 (d, 2H, J= 8.2 Hz), 6.60 (d, 2H, J=8.2 Hz), 5.07 (s, 2H), 4.84 (broad s, 1H), 3.55 (broad s, 2H), 3.37 (m, 2H), 2.67 (t, 2H, J=6.9 Hz). FAB MS m/z 271 (M+1).

Provenance & Evidence