1-Methylpiperazine → 2-Chloro-3-(4-methylpiperazin-1-YL)pyrazine

HRID 493319Notes

Reaction equation

HRID 493319 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C(#N)C>[Cl:8][C:7]1[C:2]([N:13]2[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 785752,3-Dichloropyrazine

Product 1

HCID 220363522-Chloro-3-(4-methylpiperazin-1-YL)pyrazineYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,3-dichloropyrazine (10.1 g, 68 mmol) and N-methylpiperazine (10.15 g, 100 mmol) in acetonitrile (250 mL) was stirred at room temperature for 60 h. The solvent was removed under reduced pressure and the residue was taken up in CHCl3/brine. The dried (MgSO4) organic layer was concentrated and the remaining oil was purified by chromatography on silica gel using CHCl3/MeOH (95:5) as eluent to give 10.7 g (75%) of the title compound as an oil that crystallized upon standing: mp 34-36° C. Anal. (C9H13ClN4) C, H, N.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dry with materialThe dried (MgSO4) organic layer
  3. concentrationwas concentrated
  4. customthe remaining oil was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-82c2c44ed4c64d36b80d7c03f72a40a5
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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