Cyclopentylamine → N-Cyano-N'-(3-trifluoromethylphenyl)-N"-cyclopentylguanidine

Participants

Reaction Steps

N-(3-Trifluoromethylphenyl)-N'-cyano-O-phenylisourea (1 mmol, 290 mg) was stirred for 19 h at 80° C. in cyclopentylamine (1 ml). After concentration of the cold reaction mixture, the residue was dissolved in dichloromethane, washed with 1 N aqueous HCl (2×), water, dried (Na2SO4) and concentrated. The residue was purified by column chromatography (heptane:ethyl acetate 3:1) to give the title compound (205 mg, 68%) as a syrup. Crystallisation from heptane:ethyl acetate 2:1 gave 147 mg (49%). Mp 111.5-113° C; 1H-NMR (CDCl3): δ 1.42 (m, 2H), 1.65 (m, 4H), 2.05 (m, 2H), 4.12 (sextet, 1H), 4.85 (br, 1H), 7.35 (br s,1H), 7.5 ppm (m, 4H); MA calc for C14H15F3N4 : C, 56.75%; H, 5.10%; N, 18.91%. Found: C, 56.48%; H, 5.08%; N, 18.65%.

Provenance & Evidence