Cyclohexanemethylamine → 4-[(Cyclohexylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

HRID 1296174Notes

Reaction equation

HRID 1296174 reaction equation
F[C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[CH:24]1([CH2:30][NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CCO>[CH:24]1([CH2:30][NH:31][C:2]2[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:14][C:15]([F:17])([F:16])[F:18])[CH2:9][C:10]([F:12])([F:13])[F:11])=[O:7])=[CH:4][C:3]=2[N+:21]([O-:23])=[O:22])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 76688CyclohexanemethylamineHCID 589117444-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Product 1

HCID 589117434-[(Cyclohexylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide (107 mg, 0.307 mmol) and cyclohexylmethylamine (0.050 mL, 0.368 mmol) were stirred in 3 mL of EtOH containing TEA (0.065 mL, 0.460 mmol) at 75° C. for 3 h. The mixture was concentrated. The residue was re-dissolved in EtOAc and washed with 5% KHSO4 solution, saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The title product was purified by flash chromatography using 9:1/hexanes:EtOAc. Yield: 113 mg (83%). 1H NMR (400 MHz, CDCl3) δ 1.05 (m, 2H), 1.24 (m, 4H), 1.69 (m, 2H), 1.75 (m, 2H), 1.83 (m, 1H), 3.17 (t, J=6.64 Hz, 2H), 4.23 (q, J=8.53 Hz, 4H), 6.91 (d, J=8.98 Hz, 1H), 7.51 (d, J=8.89 Hz, 1H), 8.28 (s, 1H), 8.39 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-1d40ff7a025e49b182ba417ee9d57ba9
Source dataset
uspto-grants-2007_07
Patent number
US07244850B2

Reaction notes

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