4-Cyclohexylbenzenamine → HCID 57586903, compound

Participants

Reaction Steps

A mixture of methyl 4-oxochromane-7-carboxylate (1.50 g, 7.27 mmol), 4-cyclohexylaniline (2.55 g, 14.55 mmol), decaborane (0.27 g, 2.18 mmol) in dry MeOH (15 mL) was stirred under nitrogen for 60 h. Solvent evaporation in vacuo and chromatography (8% EtOAc in Hexane) gave methyl 4-[(4-cyclohexylphenyl)amino]chromane-7-carboxylate as a slightly yellow solid. HPLC/MS: m/z=365.2 (M+1), Rt=2.56 min. 1H NMR (CDCl3): δ 7.59 (1H, dd, J=2.0 Hz, 8.0 Hz), 7.56 (1H, d, J=2.0 Hz), 7.43 (1H, d, J=8.0 Hz), 7.12 (2H, d, J=8.5 Hz), 6.69 (2H, d, J=8.5 Hz), 4.68 (1H, t, J=4.5 Hz), 4.35-4.26 (2H, m), 3.95 (3H, s), 3.86 (1H, br s), 2.46 (1H, m), 2.20 (2H, dd, J=4.5 Hz, 10.5 Hz), 1.92-1.87 (4H, m), 1.80-1.77 (1H, m), 1.43 (4H, m), 1.29 (1H, m).

Provenance & Evidence