Potassium Carbonate → 2-Chloro-3-(3-methylpiperazin-1-yl)pyrazine

HRID 1295725Notes

Reaction equation

HRID 1295725 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:9][CH:10]1[CH2:15][NH:14][CH2:13][CH2:12][NH:11]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:8][C:7]1[C:2]([N:14]2[CH2:13][CH2:12][NH:11][CH:10]([CH3:9])[CH2:15]2)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660572-MethylpiperazineHCID 785752,3-Dichloropyrazine

Product 1

HCID 534010342-Chloro-3-(3-methylpiperazin-1-yl)pyrazineYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2,3-dichloropyrazine (2.80 g, 18.8 mmol), racemic 2-methylpiperazine (1.88 g, 18.8 mmol) and K2CO3 (3.90 g, 28.2 mmol) in acetonitrile (25 mL) was heated at 65° C. for 15 h with stirring. The reaction mixture was filtered and concentrated. The crude product was purified by flash chromatography on silica gel using CHCl3/MeOH (15:1) as eluent to give 3.2 g (79%) of the title compound. MS m/z 213 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-75a52276f52c4e019e8aa1142baadad0
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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