Triethylamine → 4-Dimethylamino-N-(4-hydroxymethylbenzyl)benzamide

Participants

Reaction Steps

To a mixture of 4-(dimethylamino)benzoic acid (915 mg, 5.54 mmol) and triethylamine (772 μL, 5.54 mmol) in CH2Cl2 (25 mL) at 0° C. was added BOP-Cl (1.50 g, 6.09 mmol), and the mixture was stirred at room temperature for 20 minutes. To the reaction mixture was added (4-aminomethylphenyl)methanol (760 mg, 5.54 mmol) and triethylamine (1.54 mL, 11.08 mmol), and the mixture was stirred at room temperature overnight. To the reaction mixture was added a 50% aqueous NaHCO3 solution (50 mL), and the mixture was extracted with 5% MeOH in CHCl3 (100 mL×1, 40 mL×2). The organic layer was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by MPLC on silica gel (2% MeOH in CHCl3) to afford the titled compound (1.04 g, 66%) as a white solid.

Provenance & Evidence