Propylamine → N-(1-propyl)-4-hydroxyphenoxyacetamide

Participants

Reaction Steps

A solution of 1-propylamine (4.1 ml) and methyl 4-hydroxyphenoxyacetate (3.64 g) in methanol (50 ml) was left to stand for 72 hours at ambient temperature. The solvent was evaporated in vacuo and the residue taken up in ethyl acetate. The solution was washed sequentially with 1M HCl (2×25 ml) and brine (30 ml), dried (MgSO4) and the solvent evaporated to give N-(1-propyl)-4-hydroxyphenoxyacetamide as a red oil, NMR: 0.95(t, 3H, CH3 ), 1.55(m, 2H, CH2), 3.3(q, 2H, CH2N), 4.4(s, 2H, CH2O), 6.5-6.7(broad s, 1H, OH), 6.8(s, 4H, phenyl-H); m/e 227 (M+NH4)+, 210(M+H)+.

Provenance & Evidence