4-Methylmorpholine → n,n-Di-n-pentyl-2-methoxy-5-formylbenzamide

Beteiligte Stoffe

Reaktionsschritte

Di-n-pentylamine (873 mg, 5.55 mmol, 2 eq) was added to a solution of 2-methoxy-5-formylbenzoic acid (500 mg, 2.78 mmol, 1 eq), 1-hydroxy-7-azabenzotriazole (755 mg, 5.55 mmol, 2 eq), and N-methylmorpholine (0.83 mL, 7.58 mmol, 2.73 eq) in N,N-dimethylformamide (10 mL). To this was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.06 g, 5.55 mmol, 2 eq) and the reaction mixture stirred overnight. 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 to give the product as a pale brown oil (886 mg, 99%). 1H NMR (CDCl3) δ9.83 (s, 1H, O═C—H), 3.85 (s, 3H, OCH3), 3.52 (m, 1H, NCH2), 3.38 (m, 1H, NCH2), 2.98 (m, 2H, NCH2).

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