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

HRID 472932Notes

Reaction equation

HRID 472932 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[O:10][CH3:11])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH:16]1([CH2:22][NH2:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CCO>[CH:16]1([CH2:22][NH:23][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[O:10][CH3:11])=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]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 solution, saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by flash chromatography using 4:1/hex:EtOAc on silica gel. Yield: 1.05 g (73%); 1H NMR (400 MHz, CHLOROFORM-D) δ 1.04 (ddd, J=24.02, 12.11, 2.93 Hz, 2H), 1.25 (m, 3H), 1.69 (m, 2H), 1.76 (m, 1H), 1.79 (m, 1H), 1.83 (m, 1H), 1.86 (m, 1H), 3.14 (dd, J=6.44, 5.66 Hz, 2H), 3.78 (s, 3H), 6.46 (m, 1H), 6.84 (d, J=9.37 Hz, 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 solution, saturated NaHCO3 solution, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-80c0fdba65124b8c845826ae9eccd586
Source dataset
uspto-grants-2014_01
Patent number
US08633235B2

Reaction notes

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