Cyclohexanemethylamine → Methyl {4-[(cyclohexylmethyl)amino]-3-nitrophenyl}carbamate

HRID 1783889Notes

Reaction equation

HRID 1783889 reaction equation
[CH3:1][O:2][C:3](=[O:15])[NH:4][C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1.[CH:16]1([CH2:22][NH2:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CCO>[CH3:1][O:2][C:3](=[O:15])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:23][CH2:22][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1

Participants

4

Reactant 2

HCID 76688CyclohexanemethylamineHCID 3636899Methyl (4-fluoro-3-nitrophenyl)carbamate

Product 1

HCID 57591003Methyl {4-[(cyclohexylmethyl)amino]-3-nitrophenyl}carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl(4-fluoro-3-nitrophenyl)carbamate (1.00 g, 4.67 mmol) and cyclohexylmethyl amine (0.730 mL, 5.60 mmol) were stirred in EtOH (20 mL) containing TEA (1.0 mL, 7.00 mmol) at 75° C. for 24 h. The solvent was concentrated. The residue was dissolved in EtOAc and washed with 5% KHSO4 aqueous solution, saturated NaHCO3 aqueous solution, brine and dried over anhydrous MgSO4. The crude product was purified by flash chromatography using 4:1/hexanes:EtOAc on silica gel. Yield: 1.05 g (73%); 1H NMR (400 MHz, CHLOROFORM-D) δ 1.04 (m, 2H), 1.25 (m, 3H), 1.69 (m, 2H), 1.77 (m, 2H), 1.83 (m, 1H), 1.86 (m, 1H), 3.14 (m, 2H), 3.78 (s, 3H), 6.46 (m, 1H), 6.84 (d, J=9.37, 1H), 7.63 (m, 1H), 8.05 (d, J=2.54 Hz, 1H), 8.09 (m, 1H).

Workup

  1. concentrationThe solvent was concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 5% KHSO4 aqueous solution, saturated NaHCO3 aqueous solution, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-b7cdc726aa8545ffacfb760efffc8f3b
Source dataset
uspto-grants-2009_03
Patent number
US07501447B2

Reaction notes

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