(2-Thienylmethyl)amine → HCID 131728468, compound

Participants

Reaction Conditions

Reaction Steps

2-Aminomethyl thiophene (0.38 g, 3.363 mmol) and tetrabutylammonium iodide (0.02 g, 0.054 mmol) were added to a suspension of the carboxylic acid of Example 56k (0.4 g, 0.96 mmol) in methanol (5 mL) under nitrogen in a pressure reactor vessel and heated to 110° C. for 4 h. The reaction mixture was concentrated (oily residue), treated with methanolic HCl (15 mL) and refluxed for 3.5 h. It was concentrated, treated with an aqueous sodium bicarbonate solution to pH 8 and extracted with chloroform. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, 0.5% methanol/chloroform) to obtain the title compound. Yield: 0.21 g, (43.5%). 1H NMR (CDCl3): δ 2.68 (s, 3H, CH3), 2.98 (t, 2H, CH2), 3.18 (t, 2H, CH2), 3.9 (s, 3H, CH3), 4.6 (s, 2H, CH2), 4.67 (s, 1H, NH), 5.21 (s, 2H, CH2), 6.50 (s, 1H, Ar), 6.55 (s, 1H, Ar), 6.95 (s, 2H, Ar), 7.2 (m, 1H, Ar), 8.05 (s, 1H, Ar), 8.45 (s, 1H, Ar); MS: m/e (ES+) 505 (M+1).

Provenance & Evidence