4-Cyclohexylbenzenamine → HCID 57586903, compound

HRID 1717697Notes

Reaction equation

HRID 1717697 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[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[C:11]4[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=4)[O:5][CH2:4][CH2:3]3)=[CH:27][CH:28]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 807644-CyclohexylbenzenamineHCID 11769654Methyl 4-oxochroman-7-carboxylateHCID 178419135HCID 178419135, compound

Product 1

HCID 57586903HCID 57586903, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  1. customSolvent evaporation in vacuo and chromatography (8% EtOAc in Hexane)

Sources & evidence

ORD record
ord-f324485b40b84af1b58bbb24ba817ba5
Source dataset
uspto-grants-2010_09
Patent number
US07803951B2

Reaction notes

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