Water → N4-cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N1-phenyl-benzene-1,4-diamine

HRID 1241934Notes

Reaction equation

HRID 1241934 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:11](F)[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[CH:1]1([CH2:7][NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:11]([N:30]3[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]3)[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 21061670N4-cyclohexylmethyl-2-fluoro-5-nitro-N1-phenyl-benzene-1,4-diamine

Product 1

HCID 21061669N4-cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N1-phenyl-benzene-1,4-diamineYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N4-cyclohexylmethyl-2-fluoro-5-nitro-N1-phenyl-benzene-1,4-diamine (0.23 g, 0.66 mmol), N-methylpiperazine (0.22 mL, 1.97 mmol) and N,N′-diisopropylethylamine (0.34, 1.97 mmol) in DMF (3.0 mL) was stirred at 100° C. under an inert atmosphere for 16 h. The reaction mixture was transferred to a separatory funnel containing water. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water, brine and dried over MgSO4. The solution was filtered through diatomaceous earth and the solvent was evaporated. The resulting dark red residue was flash chromatographed (5% MeOH/CH2Cl2) to give N4-cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N1-phenyl-benzene-1,4-diamine as a red foam (0.22 g, 80.7% yield). M+, 424

Workup

  1. customThe reaction mixture was transferred to a separatory funnel
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic layers were washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered through diatomaceous earth
  6. customthe solvent was evaporated
  7. customchromatographed (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-01af52ea6a9b4085a881b35077b3bda5
Source dataset
uspto-grants-2006_10
Patent number
US07115644B2

Reaction notes

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