Cyclopentylamine → HCID 178493222, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-Cyano-N'-(3-methoxy-5-trifluoromethyl-phenyl)-O-phenylisourea (0.52 mmol, 175 mg) in dry acetonitrile (1 ml), cyclopentylamine (1.04 mmol, 0.113 ml) and triethylamine (0.080 ml) were added. The mixture was stirred for 19 h at 75° C. under nitrogen. After concentration the residue was dissolved in dichloromethane, washed with 1 N aqueous HCl (2×), water, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (ethyl acetate/heptane 1:2) to give a syrup. Crystallisation from ethyl acetate/heptane 1:4 gave grey crystals (110 mg, 65%). Mp 101-102° C.; 1H-NMR (CDCl3): δ 1.40 (m, 2H), 1.65 (m, 4H), 2.02 (m, 2H), 4.13 (sextet, 1H), 5.05 (br, 1H), 6.96 (s, 1H), 7.00 (s, 1H), 7.03 (s, 1H), 8.15 ppm (br, 1H); EI SP/MS: 326 (M+).

Provenance & Evidence