4-Methylmorpholine → N-benzyl-N-phenyl-2-benzyloxy-5-formylbenzamide

Participants

Reaction Conditions

Reaction Steps

N-Phenylbenzylamine (0.72 g, 3.9 mmol, 2 eq) was added to a solution of 2-benzyloxy-5-formylbenzoic acid (500 mg, 1.95 mmol, 1 eq), 1-hydroxy-7-azabenzotriazole (530 mg, 3.9 mmol, 2 eq), and N-methylmorpholine (0.58 mL, 5.3 mmol, 2.73 eq) in N,N-dimethylformamide (10 mL). To this was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (750 mg, 13.9 mmol, 2 eq) and the stirred reaction mixture was heated overnight at 50° C. The reaction mixture was diluted with ethyl acetate (20 mL) and washed sequentially with 10% HCl (3×20 mL), brine (20 mL), saturated aqueous sodium bicarbonate (2×20 mL) and brine (20 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica with petroleum ether:ethyl acetate (3:1) as eluent, to give the product as a white powder (300 mg, 37%). RF (petroleum ether:ethyl acetate 1:1) 0.55. 1H NMR (CDCl3) δ9.78 (s, 1H, O═C—H), 5.08 (s, 2H, OCH2Ph), 5.02 (s, 2H, NCH2Ph).

Provenance & Evidence