Sodium Carbonate → 1-(2,5-Difluorophenyl)piperazine hydrochloride

HRID 1458997Notes

Reaction equation

HRID 1458997 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7]Cl.[F:9][C:10]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:11]=1[NH2:12].C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[ClH:2].[F:9][C:10]1[CH:16]=[CH:15][C:14]([F: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 10340Sodium CarbonateHCID 677752,5-DifluoroanilineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 185452801-(2,5-Difluorophenyl)piperazine hydrochloride

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

7.0 g of bis(2-chloroethyl)amine hydrochloride was suspended in 60 ml of butanol and 5 g of 2,5-difluoroaniline was added thereto at room temperature. After heating under reflux for 72 hours, the reaction mixture was cooled and 4.1 g of sodium carbonate was added. After heating under reflux for additional 24 hours, the precipitate was taken up by filtration, dissolved in water and extracted with chloroform. Then the extract was washed successively with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was dissolved in a small amount of chloroform, converted into hydrochloride by adding a 4N hydrochloric acid/dioxane solution and filtered to thereby give 2.39 g mg of the title compound.

Workup

  1. customat room temperature
  2. temperatureAfter heating
  3. temperatureunder reflux for 72 hours
  4. temperaturethe reaction mixture was cooled
  5. temperatureAfter heating
  6. temperatureunder reflux for additional 24 hours
  7. filtrationthe precipitate was taken up by filtration
  8. dissolutiondissolved in water
  9. extractionextracted with chloroform
  10. washThen the extract was washed successively with water
  11. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  12. customAfter evaporating the solvent
  13. dissolutionthe residue was dissolved in a small amount of chloroform
  14. additionby adding a 4N hydrochloric acid/dioxane solution
  15. filtrationfiltered

Sources & evidence

ORD record
ord-af81b7983aff40b7b03a735c2f598951
Source dataset
uspto-grants-1998_12
Patent number
US05852019

Reaction notes

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