To a solution of 4-amino-N-dodecylbenzamide (0.304 g, 1.0 mmol), acetic acid (0.060 g, 1.0 mmol) and methyl 2-formylbenzoate (0.164 g, 1.0 mmol) in ethanol (2 mL) was added at once NaBH3CN (0.075 g, 1.20 mmol). The resulting mixture was stirred overnight at rt. A saturated solution of NaHCO3 (10 mL) was added to the reaction mixture, the aqueous layer was separated and extracted with DCM. The combined organic layers were dried over MgSO4, filtered and concentrated to give a colorless oil. This crude product was purified by column chromatography over silica gel to give the title compound as a colorless oil (0.212 g, 47%). M+(LC/MS(ESI)): 453.6. HPLC (Condition A), Rt: 6.64 min (HPLC purity: 100%).
