Cyclopropylamine → HCID 131728464, compound

Participants

Reaction Conditions

Reaction Steps

Cyclopropylamine (0.819 g, 1.4 mmol) and tetrabutylammonium iodide (0.010 g, 0.027 mmol) were sequentially added with stirring to a solution of the carboxylic acid of Example 56k (0.59 g, 1.2 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 a methanolic HCl solution (15 mL) and refluxed for 2 h. The reaction mixture was concentrated, treated with an aqueous sodium bicarbonate solution to pH 7, water and extracted with n-butanol. 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: 0.120 g, (22%); 1H NMR (DMSO-d6): δ 0.20 (d, 2H, CH2), 0.40 (d, 2H, CH2), 2.10 (m, 1H, CH), 2.60 (s, 3H, CH3), 2.80 (t, 2H, CH2), 3.10 (d, 2H, CH2), 3.90 (s, 3H, OCH3), 5.15 (s, 2H, CH2), 6.10 (t, 1H, NH), 6.70 (s, 1H, Ar), 6.72 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.20 (s, 1H, Ar); MS: m/e (CI+) 451 (M+1).

Provenance & Evidence