Benzylamine → HCID 131728470, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl amine (1.08 g, 10.08 mmol) and tetrabutylammonium iodide (0.02 g, 0.054 mmol) were added to a suspension of the carboxylic acid of Example 56k (0.86 g, 2.0677 mmol) in methanol (8 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 (25 mL) and refluxed overnight. 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, 1% methanol/chloroform) to obtain the title compound. Yield: 0.56 g, (54%); 1H NMR (CDCl3): δ 2.62 (s, 3H, CH3), 2.95 (t, 2H CH2), 3.2 (m, 2H, CH2), 3.83 (s, 2H, CH2), 3.9 (s, 2H, CH2), 4.95 (s, 1H, NH), 6.5 (s, 1H, Ar), 6.53 (s, 1H, Ar), 7.4 (m, 5H, Ar), 8.1 (s, 1H, Ar), 8.47 (s, 1H, Ar); MS: m/e (ES+) 501 (M+1).

Provenance & Evidence