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

HRID 230024Notes

Reaction equation

HRID 230024 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[CH:18]1([C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[B][B][B][B][B][B][B][B][B][B]>CO>[CH:18]1([C:24]2[CH:25]=[CH:26][C:27]([NH:28][CH:2]3[C:10]4[C:5](=[CH:6][C:7]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])=[CH:8][CH:9]=4)[CH2:4][CH2:3]3)=[CH:29][CH:30]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 807644-CyclohexylbenzenamineHCID 67484921Butyl 1-oxoindane-5-carboxylateHCID 178419135HCID 178419135, compound

Product 1

HCID 57586900Butyl 1-[(4-cyclohexylphenyl)amino]indane-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of butyl 1-oxoindane-5-carboxylate (2.0 g, 8.60 mmol) and 4-cyclohexylaniline (2.28 g, 20.64 mmol) in 30 mL of anhydrous MeOH was added decaborane B10H14 (0.32 g, 2.6 mmol) at room temperature under nitrogen. The resulting solution was stirred at room temperature for 1648 h. Product butyl 1-[(4-cyclohexylphenyl)amino]indane-5-carboxylate was collected by filtration as a white solid. HPLC/MS: m/z=392.3 (M+1), Rt=4.97 min. 1H NMR (CDCl3): δ 7.80 (1H, s), 7.97 (1H, d, J=8.0 Hz), 7.48 (1H, d, J=8.0 Hz), 7.14 (2H, d, J=8.5 Hz), 6.74 (2H, d, J=8.5 Hz), 5.07 (1H, t, J=7.1 Hz), 4.39 (2H, t, J=6.7 Hz), 3.92 (1H, br s), 3.10 (1H, m), 2.97 (1H, m), 2.69 (1H, m), 2.49 (1H, m), 2.02-1.80 (8H, m), 1.60-1.31 (7H, m), 1.08 (3H, t, J=7.3 Hz).

Workup

  1. filtrationProduct butyl 1-[(4-cyclohexylphenyl)amino]indane-5-carboxylate was collected by filtration as a white solid

Sources & evidence

ORD record
ord-743de3116fac44b1bbd959d38dfdb039
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

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