1,2-Diaminocyclohexane, cis- → HCID 90355899, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-4-fluorobenzonitrile (5.0 g, 37 mmol) and cis-cyclohexane-1,2-diamine (12.6 g, 111 mmol) was heated to 120° C. After 48 hours, the reaction mixture was cooled to ambient temperature and purified directly via silica gel chromatography (1-5% methanol/dichloromethane, linear gradient) to afford rel-2-amino-4-{[(1R,2S)-2-aminocyclohexyl]amino}benzonitrile. MS ESI calc'd. for C13H19N4 [M+H]+ 231. Found 231. 1H NMR (400 MHz, CDCl3) δ 7.13 (d, J=8.8 Hz, 1H), 6.01 (d, J=9.6 Hz, 1H), 5.85 (s, 1H), 4.68 (d, J=9.6 Hz, 1H), 4.22 (br s, 2H), 3.39-3.34 (m, 1H), 3.14-3.11 (m, 1H), 1.70-1.35 (m, 10H).

Provenance & Evidence