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

HRID 329888Notes

Reaction equation

HRID 329888 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:24](Br)[CH2:25][OH:26]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][N:10]([CH2:24][CH2:25][OH:26])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazine

Product 1

HCID 105125282-[4-(Pyridin-2-yl)piperazin-1-yl]ethan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-(2-pyridyl)piperazine (5 g), potassium carbonate powder (9 g) and N,N-dimethylformamide (30 ml) was added dropwise ethylene bromohydrin (5.74 g) under stirring. The mixture was stirred at room temperature for 6 hours, diluted with water (100 ml) and extracted with chloroform. The chloroform layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was purified by silica gel chromatography [eluent: dichloromethane-methanol (95:5)] to give 4-(2-pyridyl)-1-piperazineethanol as crystals, m.p. 82.5°-84° C. Yield 4.68 g (73.7%).

Workup

  1. stirringThe mixture was stirred at room temperature for 6 hours
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel chromatography [eluent: dichloromethane-methanol (95:5)]

Sources & evidence

ORD record
ord-44d5b29f22d548d6aa2835fc66fedf15
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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