Dimethylamine → 2-(4-Aminophenyl)-N,N-dimethylacetamide

Participants

Reaction Steps

A suspension of 4-aminophenylacetic acid (5 g, 30 mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (6.9 g, 36 mmol), and dimethylamine (6.5 mol of a 5.6M solution in EtOH 36 mmol) in 1,2, DCE was stirred at room temperature for 4 h. Silica was added, the suspension evaporated and residue loaded onto silica plug column, eluting with DCM:MeOH/98:2). The title compound (2.6 g, 45%) was isolated as an orange solid. 1H MNR (400 MHz, CDCl3) δ2.94 (3H, s), δ2.98 (3H, s), 3.60 (2H, s), 6.64 (2H, d, J=8.3 Hz), 7.03 (2H, d, 8.2 Hz). MS (CI)+179 (M+H)+.

Provenance & Evidence