Dimethylformamide → 1-Piperazineethanol, 4-(3-chlorophenyl)-

HRID 746243Notes

Reaction equation

HRID 746243 reaction equation
[CH2:1](Br)[CH2:2][OH:3].Cl.[Cl:6][C:7]1[CH:8]=[C:9]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:6][C:7]1[CH:8]=[C:9]([N:13]2[CH2:18][CH2:17][N:16]([CH2:1][CH2:2][OH:3])[CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 256811-(3-Chlorophenyl)piperazine monohydrochloride

Product 1

HCID 967031-Piperazineethanol, 4-(3-chlorophenyl)-Yield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethylene bromohydrin (5.4 g) was added dropwise to a mixture of 1-(3-chlorophenyl)piperazine hydrochloride (5 g), potassium carbonate powder (12 g) and N,N-dimethylformamide (35 ml) with stirring. The mixture was further stirred at room temperature overnight, then 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 Na2SO4. The solvent was distilled off and the residue was purified by silica gel chromatography [eluent: ethyl acetate-methanol (4:1)] to give 4.06 g (78.6%) of 4-(3-chlorophenyl)-1-piperazineethanol as an oil.

Workup

  1. stirringThe mixture was further stirred at room temperature overnight
  2. extractionextracted with ethyl ether
  3. washThe ethyl ether layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over Na2SO4
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel chromatography [eluent: ethyl acetate-methanol (4:1)]

Sources & evidence

ORD record
ord-d59b809d03444a6cb96c5419613064fc
Source dataset
uspto-grants-1986_07
Patent number
US04603135

Reaction notes

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