Furfurylamine → HCID 131728466, compound

Participants

Reaction Conditions

Reaction Steps

Freshly distilled furfurylamine (0.58 g, 0.60 mmol) and tetrabutylammonium iodide (0.010 g, 0.027 mmol) were sequentially added with stirring to a solution of Example 56k (0.5 g, 1.20 mmol) in dry methanol (10 mL). The reaction mixture was stirred at 110° C. for 5 h in an atmosphere of nitrogen. It was concentrated, treated with methanolic HCl solution (15 mL), refluxed overnight, concentrated, treated with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.438 g, (84.88%); 1H NMR (DMSO-d6): δ 1.70 (s, 2H, CH2), 2.30 (m, 6H, 3CH2), 2.65 (s, 3H, CH3), 3.05 (q, 2H, CH2), 3.60 (t, 2H, CH2), 3.90 (s, 3H, OCH3), 5.10 (s, 2H, CH2), 6.25 (t, 1H, NH), 6.70 (s, 1H, Ar), 6.70 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.15 (s, 1H, Ar); MS (CI+): m/e (ES+) 490 (M+1).

Provenance & Evidence