p-Fluoronitrobenzene → 4-[4-(4-Nitrophenyl)piperazin-1-yl]phenol

HRID 414241Notes

Reaction equation

HRID 414241 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>O>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=3)[CH2:6][CH2:5]2)=[CH:16][CH:17]=1)([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 92467p-(1-Piperazinyl)phenol

Product 1

HCID 113810174-[4-(4-Nitrophenyl)piperazin-1-yl]phenolYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 91.7 parts of 4-(1-piperazinyl)phenol, 71.0 parts of 1-fluoro-4-nitrobenzene, 60.0 parts of potassium carbonate and 450 parts of N,N-dimethylacetamide was stirred over weekend at room temperature. Water was added and after standing for 5 hours, the product was filtered off. It was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 114.4 parts (76%) of 4-[4-(4-nitrophenyl)-1-piperazinyl]phenol; mp. 260.0° C. (intermediate 9).

Workup

  1. filtrationthe product was filtered off
  2. customIt was purified by column chromatography over silica gel
  3. customThe pure fractions were collected
  4. customthe eluent was evaporated

Sources & evidence

ORD record
ord-65f369ebf2fb4e74a62466c2ab3c178a
Source dataset
uspto-grants-1988_12
Patent number
US04791111

Reaction notes

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