2-Pyridineethanamine → HCID 131728465, compound

Participants

Reaction Conditions

Reaction Steps

2-(2-Aminoethyl)pyridine (8.13 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 (0.7 g, 1.62 mmol) in dry methanol (10 mL). The reaction mixture was stirred at 110° C. for 7 h in an atmosphere of nitrogen. It was concentrated and treated with a methanolic HCl solution (10 mL), refluxed overnight, concentrated, treated water and 10% aqueous sodium bicarbonate solution to pH 7. The solid that precipitated was filtered, washed with water, dried and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.225 g, (26.81%). 1H NMR (DMSO-d6): δ 2.70 (s, 3H, CH3), 3.0-3.10 (m, 6H, 3CH2), 3.40-3.55 (m, 2H, CH2), 3.90 (s, 3H, OCH3), 5.20 (s, 2H, CH2), 6.45 (t, 1H, NH), 6.80 (s, 1H, Ar), 6.83 (s, 1H, Ar), 7.30-7.50 (m, 3H, Ar), 7.80 (t, 1H, Ar), 8.20 (s, 1H, Ar), 8.25 (s, 1H, Ar); MS (CI+): m/e 516 (M+1).

Provenance & Evidence