2,5-Dichloroaniline → 1-(2,5-dichlorophenyl)piperazine hydrochloride

HRID 1458998Notes

Reaction equation

HRID 1458998 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7]Cl.[Cl:9][C:10]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:11]=1[NH2:12].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[ClH:2].[Cl:9][C:10]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:11]=1[N:12]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 72622,5-DichloroanilineHCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 127857591-(2,5-dichlorophenyl)piperazine hydrochlorideYield 13.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

7.14 g of bis(2-chloroethyl)amine hydrochloride was suspended in 70 ml of butanol and 6.48 g of 2,5-dichloroaniline was added thereto at room temperature. After heating under reflux for 48 hours, the reaction mixture was cooled and 5.52 g of potassium carbonate was added. After heating under reflux for additional 24 hours, the insoluble matters were filtered off and the filtrate was concentrated. Then the obtained residue was extracted with chloroform and a saturated aqueous solution of sodium hydrogencarbonate. The extract was 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 (100 g, chloroform:methanol=50:1-30:1). The product was converted into hydrochloride by adding a 1N hydrochloric acid/ethanol solution to thereby give 1.41 g of the title compound.

Workup

  1. customat room temperature
  2. temperatureAfter heating
  3. temperatureunder reflux for 48 hours
  4. temperaturethe reaction mixture was cooled
  5. temperatureAfter heating
  6. temperatureunder reflux for additional 24 hours
  7. filtrationthe insoluble matters were filtered off
  8. concentrationthe filtrate was concentrated
  9. extractionThen the obtained residue was extracted with chloroform
  10. washThe extract was washed with water
  11. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  12. customAfter evaporating the solvent
  13. customthe residue was purified by silica gel column chromatography (100 g, chloroform:methanol=50:1-30:1)
  14. additionby adding a 1N hydrochloric acid/ethanol solution

Sources & evidence

ORD record
ord-0be737b309034d8b8962d841a2ca1bb1
Source dataset
uspto-grants-1998_12
Patent number
US05852019

Reaction notes

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