Water → 1-(3-Nitrophenyl)piperazine

HRID 1292841Notes

Reaction equation

HRID 1292841 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].O>CS(C)=O>[N+:14]([C:9]1[CH:8]=[C:13]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:12]=[CH:11][CH:10]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 27602161-(3-Nitrophenyl)piperazineYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

28.4 g (0.33 mol, 5.5 eq) of piperazine is dissolved in 50 ml of DMSO. 6.4 ml (60 mmol) of 2-fluoronitrobenzene is added. The mixture is heated at 100° C. for 60 hours. After cooling, the reaction mixture is transferred into 530 ml of water. The precipitate formed is filtered and the filtrate extracted with Et2O. After drying on MgSO4 and concentration under vacuum, the crude product is purified by column chromatography (eluent CH2Cl2/MeOH 9:1) to produce 8.04 g of the expected compound in the form of an orange oil which crystallizes at room temperature (yield: 65%).

Workup

  1. temperatureAfter cooling
  2. customThe precipitate formed
  3. filtrationis filtered
  4. extractionthe filtrate extracted with Et2O
  5. customAfter drying on MgSO4 and concentration under vacuum
  6. customthe crude product is purified by column chromatography (eluent CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-d7833dd5e71643e8847d4e58b69c24d7
Source dataset
uspto-grants-2007_07
Patent number
US07238693B2

Reaction notes

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