Benzylamine → N-benzyl-2,2-dimethoxypropionamide

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2,2-dimethoxypropionate (2.33 g, 15.7 mmol) and benzylamine (1.68 g, 15.7 mmol) in a 20 mL screw-capped vial was stirred at 55° C. for 12 d. To the reaction mixture, which mostly solidified upon cooling to ambient temperature was added hexane (5 mL), and the mixture was sonicated and stirred vigorously. The solid was filtered off, washed with hexanes, and dried in vacuo to give the title compound as off-white solid. 1H NMR (400 MHz, CDCl3): δ=7.38-7.25 (m, 5H), 7.08 (brs, 1H), 4.49 (d, J=5.6 Hz, 2H), 3.25 (s, 6H), 1.52 (s, 3H). MS(ES+): m/z=246.07 (58) [MNa+], 224.11 (58) [MH+], 192.12 (100) [MH+-MeOH], 160.11 (33) [MH+-2 MeOH]. HPLC: tR=2.78 min (polar—5 min, ZQ3).

Provenance & Evidence