Piperazine → 1-(4,6-Dimethylpyridin-2-YL)piperazine

HRID 1910810Notes

Reaction equation

HRID 1910810 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>CS(C)=O.O>[CH3:8][C:6]1[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 125083782-Chloro-4,6-dimethylpyridine

Product 1

HCID 233680631-(4,6-Dimethylpyridin-2-YL)piperazineYield 52%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 2-chloro-4,6-dimethyl-pyridine (1 g, 7.09 mmol) and piperazine (2 g, 23.2 mmol) in DMSO was heated at 140° C. for 24 h. The mixture was allowed to cool, diluted with water and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue which was purified by column chromatography on silica gel (60-120 mesh), eluting with 5% methanol/chloroform to afford 1-(4,6-dimethyl-pyridin-2-yl)-piperazine (0.7 g, 52%).

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customwas purified by column chromatography on silica gel (60-120 mesh)
  8. washeluting with 5% methanol/chloroform

Sources & evidence

ORD record
ord-6dcdca307b18444ab0bc0f89c838a68e
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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