4-Methylmorpholine → HCID 22244748, compound

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Reaction Steps

N-(t-Butoxycarbonyl)ethylenediamine 2 (5 mmol, 800 mg) was weighed directly into a clean dry flask, which was then tightly stoppered. 3-Acetylbenzoic acid 3 (5 mmol, 820 mg) was added directly to the amine in the flask. Under an inert atmosphere dry dimethylformamide (15 mL) was added to the flask. Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (5 mmol, 2.21 g) was added to the solution, and subsequently N-methylmorpholine (15 mmol, 1.51 g, 1.7 mL) was added to the solution, and the mixture was allowed to stir for 2-3 hrs. The reaction mixture was quenched by the addition of 15 mL of water to the reaction flask, and partitioned between water (300 mL) and ethyl acetate (300 mL). The organic phase was washed successively with saturated sodium bicarbonate (200 mL), water (4×300 mL), and brine (200 mL) and then dried over anhydrous sodium sulfate. Filtering off the drying agent and concentration of the organic phase to ˜10-15 mL yielded a tan solid. Hexanes (˜30 mL) were added and the mixture gently heated to reflux. Upon cooling semicrystalline product was precipitated as a white powder. The product was collected by filtration and dried. Yield 775 mg, 51%.

Provenance & Evidence