Piperazine → 1-(3-Fluorophenyl)piperazine

HRID 459813

Reaction equation

HRID 459813 reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][CH:7]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 4837PiperazineHCID 140821-Bromo-3-fluorobenzeneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 774181-(3-Fluorophenyl)piperazine

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1 g (5.71 mmol) of 3-fluorobromobenzene and 2.95 g (34.29 mmol) of piperazine are dissolved in 20 ml of toluene, and 0.77 g (8 mmol) of sodium tert-butoxide is added. In the presence of 0.11 g (0.17 mmol) of BINAP and 0.05 g (0.06 mmol) of tris(dibenzylideneacetone)dipalladium, the mixture is then stirred under reflux overnight. After cooling, ethyl acetate is added and the mixture is washed with water. The mixture is then extracted with 1N hydrochloric acid, and the aqueous phase is washed with ethyl acetate. The pH is adjusted to 8–9 and the mixture is then extracted with dichloromethane. The organic phase is dried over magnesium sulphate and the solvent is removed, giving the target compound.

Workup

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. washthe mixture is washed with water
  4. extractionThe mixture is then extracted with 1N hydrochloric acid
  5. washthe aqueous phase is washed with ethyl acetate
  6. extractionthe mixture is then extracted with dichloromethane
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. customthe solvent is removed
  9. customgiving the target compound

Sources & evidence

ORD record
ord-83ceb8398b0a4c5a9a0c9f3f58d2e4e7
Source dataset
uspto-grants-2007_03
Patent number
US07196086B2

Linked notes

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