Dimethylformamide → 2-[4-(4-Fluorophenyl)piperazin-1-yl]ethan-1-ol

HRID 329883Notes

Reaction equation

HRID 329883 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:25](Br)[CH2:26][OH:27]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:25][CH2:26][OH:27])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 752601-(4-Fluorophenyl)piperazine

Product 1

HCID 134588432-[4-(4-Fluorophenyl)piperazin-1-yl]ethan-1-olYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-(4-fluorophenyl)piperazine (7.24 g), potassium carbonate powder (13.9 g) and N,N-dimethylformamide (30 ml) was added dropwise ethylene bromohydrin (10.0 g) under stirring. The mixture was stirred at room temperature for 3 hours, diluted with 100 ml of water and extracted with ethyl ether. The ethyl ether layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was purified by silica gel chromatography [eluent: hexane-ethyl acetate (1:3)] to give 7.12 g (79.0%) of 4-(4-fluorophenyl)-1-piperazineethanol as an oil. IR(Neat): 3150 cm-1. NMR (CDCl3)δ: 2.47-2.80(6H, m), 2.97-3.20(4H, m), 3.10(1H, s), 3.65(2H, t, J=5.5), 6.71-7.13(4H, m).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. extractionextracted with ethyl ether
  3. washThe ethyl ether layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel chromatography [eluent: hexane-ethyl acetate (1:3)]

Sources & evidence

ORD record
ord-2ad8a524b41147a69c92b494d42c9874
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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