Cyclohexylamine → Ammonia

Participants

Reaction Steps

A mixture of 4-(2-hydroxy-3-isopropylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (A. N. Grinev et al., Otkrytiya, Izobret. 1986, (43), 275) (10 mg) and cyclohexylamine (50 μl) was heated at 175° C. for 11 hours. The reaction mixture was dissolved in ethyl acetate and washed with 0.1 N HCl 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-(2-hydroxy-3-isopropylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid cyclohexylamide (7 mg) as a white powder. FAB-MS: m/z 389 (MH+); 1H-NMR (CDCl3): δ 1.10 (6H, d, J=6 Hz), 1.20-2.04 (10H, m), 2.78 (3H, s), 2.83 (1H, m), 2.87 (1H, dd, J1=12.5 Hz, J2=6 Hz), 2.97 (1H, dd, J1=12.5 Hz, J2=3 Hz), 3.97 (1H, m), 4.08 (3H, m), 6.45 (1H, br d, J=8 Hz), 6.64 (1H, d, J=8 Hz), 7.04 (1H, d, J=8 Hz), 7.27 (1H, t, J=8 Hz).

Provenance & Evidence