4-Cyclohexylbenzenamine → Butyl 1-[(4-cyclohexylphenyl)amino]indane-5-carboxylate

Participants

Reaction Steps

A mixture of butyl 1-oxoindane-5-carboxylate (2.00 g, 8.60 mmol), 4-cyclohexylaniline (2.28 g, 13.00 mmol), decaborane (0.32 g, 2.60 mmol) in dry MeOH (30 mL) was stirred under nitrogen for 60 h. Yellow precipitates were collected by filtration and washed with MeOH (3×5 mL) to give butyl 1-[(4-cyclohexylphenyl)amino]indane-5-carboxylate as a white solid. HPLC/MS: m/z=392.6 (M+1), Rt=4.97 min. 1H NMR (CDCl3): δ 8.00 (1H, s), 7.97 (1H, d, J=8.0 Hz), 7.48 (1H, d, J=8.0 Hz), 7.14 (2H, d, J=8.0 Hz), 6.74 (2H, d, J=8.0 Hz), 5.07 (1H, t, J=7.0 Hz), 4.39 (2H, t, J=6.5 Hz), 3.92 (1H, br s), 3.12-3.07 (1H, m), 3.00-2.94 (1H, m), 2.72-2.66 (1H, m), 2.52-2.47 (1H, m), 2.02-1.80 (8H, m), 1.60-1.31 (7H, m), 1.08 (3H, t, J=7.5 Hz).

Provenance & Evidence