p-Anisoyl chloride → HCID 1744311, compound

Participants

Reaction Steps

To a solution of p-methoxybenzoyl chloride (37.8 g, 0.222 mol) in CH2Cl2 (200 ml) at 0°, is added triethylamine (22.5 g, 0.222 mol) followed by the slow addition of 3-phenylpropylamine (20 g, 0.148 mol) dissolved in CH2Cl2 (100 ml). The reaction is allowed to warm to room temperature over several hours. The solvent is removed in vacuo, and the residue is dissolved in EtOAc (500 ml) and 2N HCl (500 ml). The EtOAc is separated, washed with 2N HCl (350 ml), H2O (350 ml), saturated NaHCO3 solution (350 ml), and saturated NaCl solution (350 ml); dried over MgSO4 ; and evaporated. The resulting light brown solid is purified by chromatography (SiO2 ; 1:9 EtOAc/hexanes, 1:4 EtOAc/hexanes) yielding N-(3-phenylpropyl)-4-methoxybenzamide as creamy solid.

Provenance & Evidence