Piperazine → 1-Piperazinylpyrazine

HRID 2376649Notes

Reaction equation

HRID 2376649 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[CH:13]=[N:12][CH:11]=[CH:10][N:9]=1.C([O-])([O-])=O.[K+].[K+]>CCO>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[N:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:8]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 73277Chloropyrazine

Product 1

HCID 27346391-Piperazinylpyrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3 g of piperazine, 1.04 ml of 2-chloropyrazine and 1.85 g of K2CO3 in 100 ml of EtOH is heated at reflux for 48 hours. The reaction mixture is concentrated under vacuum, the residue is taken up in water, the system is rendered alkaline to pH=10 by addition of 10% NaOH and subjected to extraction with chloroform, the organic phase is washed with water and dried over Na2SO4 and the solvent is evaporated under vacuum. This gives 1.8 g of the expected product following recrystallization from hexane.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 48 hours
  3. concentrationThe reaction mixture is concentrated under vacuum
  4. additionby addition of 10% NaOH
  5. extractionsubjected to extraction with chloroform
  6. washthe organic phase is washed with water
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated under vacuum
  9. customrecrystallization from hexane

Sources & evidence

ORD record
ord-4fd18d1f8dde4c6e99d9d6493448b163
Source dataset
uspto-grants-2008_12
Patent number
US07468368B2

Reaction notes

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