Water → HCID 14998803, compound

HRID 728925Notes

Reaction equation

HRID 728925 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]([CH2:20][OH:21])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].F[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1.O>CN(C)C=O.C(Cl)Cl>[N+:31]([C:28]1[CH:29]=[CH:30][C:25]([O:21][CH2:20][CH:9]2[CH2:8][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11][N:10]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:26][CH:27]=1)([O-:33])=[O:32]

Participants

7

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 14998802HCID 14998802, compound

Product 1

HCID 14998803HCID 14998803, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Suspend 4-phenyl-1-(phenylmethyl)-2-piperazinemethanol (7.8 g, 27.6 mmol) in dimethylformamide under nitrogen and add 60% sodium hydride (1.22 g, 30.4 mmol). Stir for 20 h as solid slowly dissolves. Add 1-fluoro-4-nitrobenzene (4.29 g, 30.4 mmol) and stir at room temperature. Monitor the progress of the reaction by thin-layer chromatography. Upon completion of the reaction, add water (100 mL) to the reaction mixture andextract with methylene chloride (2×100 mL). Remove the solvent in vacuo and recrystallize the residue from ethyl acetate/hexanes (1/1) (80 mL) to provide the title compound.

Workup

  1. dissolutionslowly dissolves
  2. customMonitor the progress of the reaction by thin-layer chromatography
  3. customUpon completion of the reaction
  4. customRemove the solvent in vacuo
  5. customrecrystallize the residue from ethyl acetate/hexanes (1/1) (80 mL)

Sources & evidence

ORD record
ord-1810610852b14991991ca5d534814048
Source dataset
uspto-grants-1991_09
Patent number
US05051422

Reaction notes

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