Phenethylamine → Ammonia

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(3-(1-benzyl-piperidin-4-ylamino)-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (the compound in Example 100, 15 mg) and phenethylamine (50 μl) was heated at 170° C. for four hours. The reaction mixture was dissolved in ethyl acetate and washed with saturated ammonium chloride solution and water. The organic solvent was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography (using dichloromethane:MeOH:ammonia solution (25-28%)=10:1:0.2 as a developing solvent) to give 4-[3-(1-benzyl-piperidin-4-ylamino)-propoxy]-3-methyl-benzofuran-2-carboxylic acid phenethyl-amide (9 mg) as a colorless oil. EI-MS: m/z 525 (M+); 1H-NMR (CDCl3): δ 1.41 (2H, m), 1.85-2.09 (6H, m), 2.51 (1H, m), 2.78 (3H, s), 2.90 (6H, m),3.50 (2H, s), 3.70 (2H, q, J=7 Hz), 4.14 (2H, t, J=6 Hz), 6.61 (1H, d, J=8 Hz), 6.63 (1H, br s), 6.97 (1H, d, J=8 Hz), 7.28 (11H, m).

Provenance & Evidence