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

HRID 1717695Notes

Reaction equation

HRID 1717695 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

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).

Workup

  1. customYellow precipitates
  2. filtrationwere collected by filtration
  3. washwashed with MeOH (3×5 mL)

Sources & evidence

ORD record
ord-bfd5f6ad7e8a4beb938798886a5d7265
Source dataset
uspto-grants-2010_09
Patent number
US07803951B2

Reaction notes

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