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

Participants

Reaction Conditions

Reaction Steps

2-Amino-4-fluorobenzonitrile (200 mg, 1.47 mmol) and cis-cyclohexane-1,2-diamine (839 mg, 7.35 mmol) (Sigma-Aldrich; CAS: 1436-59-5) were added to a vial. The vial was then sealed and heated at 100° C. After 16 hours, the reaction mixture was cooled to room temperature and purified directly by silica gel chromatography (10-100% (10% methanol in DCM)/hexanes, 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 (500 MHz, DMSO-d6) δ 6.97 (d, J=8.6 Hz, 1H), 5.97 (d, J=8.6 Hz, 1H), 5.89 (d, J=1.8 Hz, 1H), 5.85 (d, J=7.7 Hz, 1H), 5.48 (s, 2H), 3.32-3.19 (m, 1H), 3.15 (s, 2H), 3.03-2.90 (m, 1H), 1.64-1.33 (m, 6H), 1.33-1.14 (m, 2H).

Provenance & Evidence