Sodium Hydroxide → 1-(4-fluoro-2-nitrophenyl)piperazine

HRID 1282079Notes

Reaction equation

HRID 1282079 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[N+:17]([O-:19])=[O:18])[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+]>Cl>[F:16][C:13]1[CH:14]=[CH:15][C:10]([N:7]2[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]2)=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2915197HCID 2915197, compound

Product 1

HCID 27374351-(4-fluoro-2-nitrophenyl)piperazineYield 66.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 1-acetyl-4-(4-fluoro-2-nitrophenyl)piperazine (10 g) was added 1.2N hydrochloric acid (190 ml) and the mixture was refluxed under heating for 17 hr. The reaction mixture was made alkaline (pH 12) with an aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a red oil. The oil was crystallized from ethyl acetate-isopropyl ether-hexane to give the title compound (5.6 g) as a red solid.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 17 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customto give a red oil
  8. customThe oil was crystallized from ethyl acetate-isopropyl ether-hexane

Sources & evidence

ORD record
ord-2b517e05e2e947339ea6c7fc6614b671
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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