Triethylamine → HCID 57591001, compound

HRID 1783900Notes

Reaction equation

HRID 1783900 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH:18]1([CH2:24][NH2:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C(N(CC)CC)C>CCO>[CH:18]1([CH2:24][NH:25][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=2[N+:15]([O-:17])=[O:16])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 3702406HCID 3702406, compound

Product 1

HCID 57591001HCID 57591001, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-Fluoro-3-nitrophenyl)-2,2-dimethylpropanamide (158 mg, 0.658 mmol) and cyclohexylmethylamine (0.100 mL, 0.790 mmol) were stirred in 3 mL of EtOH containing triethylamine (0.140 mL, 0.987 mmol) at 75° C. for 24 h. The solvent was evaporated. The residue was dissolved in EtOAc and washed with 5% KHSO4 solution, saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. Yield: 217 mg (99%). 1H NMR (400 MHz, CHLOROFORM-D): δ 0.98-1.09 (m, 2H), 1.17-1.28 (m, 3H), 1.31 (s, 9H), 1.65-1.73 (m, 2H), 1.74-1.80 (m, 2H), 1.82-1.84 (m, 1H), 1.85-1.88 (m, 1H), 3.15 (dd, J=6.64, 5.47 Hz, 2H), 6.83 (d, J=9.37 Hz, 1H), 7.23 (br.s, 1H), 7.82 (dd, J=9.18, 2.54 Hz, 1H), 8.10 (d, J=2.54 Hz, 1H), 8.11-8.13 (m, 1H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 5% KHSO4 solution, saturated NaHCO3 solution, brine
  4. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-473ac90a2b0d4fa7a2f6d8d1489c704b
Source dataset
uspto-grants-2009_03
Patent number
US07501447B2

Reaction notes

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