3-Nitroaniline → 1-(3-Nitrophenyl)piperazine

HRID 1458991Notes

Reaction equation

HRID 1458991 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].Cl.Cl[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 74233-NitroanilineHCID 10340Sodium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 27602161-(3-Nitrophenyl)piperazineYield 53.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

50 ml of a solution of 5 g of 3-nitroaniline and 6.46 g of bis(2-chloroethyl)amine hydrochloride in 1-butanol was heated under reflux for 25 hours. After adding 3.84 g of sodium carbonate, the mixture was further heated under reflux for 60 hours. After allowing to cool, the insoluble matters were collected by filtration, suspended in an aqueous solution of sodium hydroxide and extracted with chloroform. The extract was successively washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (chloroform:methanol=100:3). Thus 4.03 g of the title compound was obtained in the form of a red oily product.

Workup

  1. temperatureunder reflux for 25 hours
  2. temperaturethe mixture was further heated
  3. temperatureunder reflux for 60 hours
  4. temperatureto cool
  5. filtrationthe insoluble matters were collected by filtration
  6. extractionextracted with chloroform
  7. washThe extract was successively washed with water
  8. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  9. customAfter evaporating the solvent
  10. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:3)

Sources & evidence

ORD record
ord-33d563de7fbf442dbecf5cfb0b8cc044
Source dataset
uspto-grants-1998_12
Patent number
US05852019

Reaction notes

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