4-Cyclohexylbenzenamine → Methyl 5-[(4-cyclohexylphenyl)amino]-5,6,7,8-tetrahydronaphthalene-2-carboxylate

HRID 1717696Notes

Reaction equation

HRID 1717696 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2.[CH:16]1([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[B][B][B][B][B][B][B][B][B][B]>CO>[CH:16]1([C:22]2[CH:23]=[CH:24][C:25]([NH:26][CH:2]3[CH2:11][CH2:10][CH2:9][C:8]4[CH:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]3=4)=[CH:27][CH:28]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 807644-CyclohexylbenzenamineHCID 15309116Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylateHCID 178419135HCID 178419135, compound

Product 1

HCID 57586902Methyl 5-[(4-cyclohexylphenyl)amino]-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (1.2 g, 5.9 mmol), 4-cyclohexylaniline (2.1 g, 11.8 mmol), decaborane (0.22 g, 1.8 mmol) in dry MeOH (20 mL) was stirred under nitrogen for 4 h. Solvent evaporation and chromatography (5% to 20% EtOAc in Hexane) gave methyl 5-[(4-cyclohexylphenyl)amino]-5,6,7,8-tetrahydronaphthalene-2-carboxylate as a yellow solid. HPLC/MS: m/z=364.2 (M+1), Rt=2.83 min. 1H NMR (CDCl3): δ 7.86 (1H, s), 7.85 (1H, d, J=7.5 Hz), 7.54 (1H, d, J=7.5 Hz), 7.11 (2H, d, J=8.5 Hz), 6.68 (2H, d, J=8.5 Hz), 4.66 (1H, t, J=5.5 Hz), 3.96 (3H, s), 3.79 (1H, br s), 2.97-2.82 (2H, m), 2.46 (1H, m), 2.10-1.78 (9H, m), 1.44 (4H, m), 1.30 (1H, m).

Workup

  1. customSolvent evaporation and chromatography (5% to 20% EtOAc in Hexane)

Sources & evidence

ORD record
ord-776b0da315bc40699b02606b5bac04e6
Source dataset
uspto-grants-2010_09
Patent number
US07803951B2

Reaction notes

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