p-Fluoronitrobenzene → 1-Acetyl-4-(4-nitrophenyl)piperazine

HRID 871852Notes

Reaction equation

HRID 871852 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)(=[O:13])[CH3:12]>C(#N)C.O.C(OCC)(=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:17]2[CH2:18][CH2:19][N:14]([C:11](=[O:13])[CH3:12])[CH2:15][CH2:16]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 837951-Acetylpiperazine

Product 1

HCID 28651491-Acetyl-4-(4-nitrophenyl)piperazineYield 88.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.0 g (35.44 mmol) of 1-fluoro-4-nitrobenzene and 4.99 g (38.98 mmol) of N-acetylpiperazine in 50 mL of acetonitrile is heated at 60°C. for 15 hours. The resulting mixture is diluted with water and with ethyl acetate. After separation of the phases by settling and extraction of the aqueous phase with ethyl acetate, the organic phases are combined, dried over Na2SO4, filtered and concentrated under vacuum. 7.7 g of the expected product are obtained in the form of a yellow solid, which is used as obtained in the following step. Yield=88.8%.

Workup

  1. customAfter separation of the phases
  2. extractionextraction of the aqueous phase with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b34b531868a34a4f863d3756b6cf6cba
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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