Water → 3-Ethyl-2,5-difluoro-4-(4-methyl-1-piperazinyl)nitrobenzene

HRID 1638686Notes

Reaction equation

HRID 1638686 reaction equation
[CH2:1]([C:3]1[C:4]([F:14])=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=[C:7]([F:10])[C:8]=1F)[CH3:2].O.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C(O)C.C(N(CC)CC)C>[CH2:1]([C:3]1[C:4]([F:14])=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=[C:7]([F:10])[C:8]=1[N:20]1[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH2:19]1)[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 531671-Methylpiperazine2×HCID 148346773-Ethyl-2,4,5-trifluoro-nitrobenzene

Product 1

HCID 198411213-Ethyl-2,5-difluoro-4-(4-methyl-1-piperazinyl)nitrobenzene

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8471TriethylamineSolvent

Procedure

To 3-ethyl-2,4,5-trifluoro-nitrobenzene (1.02 g) are added ethanol (4.5 ml) and water (0.5 ml) and the mixture is stirred. To the mixture is added with stirring a mixture of 1-methylpiperazine (0.83 ml), triethylamine (1.0 ml) and ethanol (0.6 ml), and the mixture is refluxed for 5 hours. To the reaction mixture is further added 1-methylpiperazine (1.0 ml), and the mixture is refluxed for 3 hours. The mixture is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography (solvent, methylene chloride) to give 3-ethyl-2,5-difluoro-4-(4-methyl-1-piperazinyl)nitrobenzene (1.12 g), as yellow oil.

Workup

  1. additionTo the mixture is added
  2. stirringwith stirring
  3. temperaturethe mixture is refluxed for 5 hours
  4. temperaturethe mixture is refluxed for 3 hours
  5. concentrationThe mixture is concentrated under reduced pressure
  6. customthe resulting residue is purified by silica gel column chromatography (solvent, methylene chloride)

Sources & evidence

ORD record
ord-2f346a1d8b1d4149993b9b2ac168d393
Source dataset
uspto-grants-1989_11
Patent number
US04880806

Reaction notes

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