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

HRID 1295709Notes

Reaction equation

HRID 1295709 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(=O)([O-])[O-].[K+].[K+].CCCCCC>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

6

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 785752,3-Dichloropyrazine

Product 1

HCID 220363522-Chloro-3-(4-methylpiperazin-1-YL)pyrazineYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,3-dichloropyrazine (5.0 g, 34 mmol), N-methylpiperazine (5.1 g, 51 mmol) and potassium carbonate (7.0 g, 51 mmol) in acetonitrile (100 mL) was stirred at ambient temperature for 2 h. Addition of hexane, followed by filtration and concentration of the filtrate gave 7.3 g of the crude product as an orange liquid. Purification by filtration through silica using heptane/EtOAc (3:1) followed by EtOAc/acetone (1:1) gave 4.1 g (57%) of the title compound as a yellow oil which solidified upon cooling. HPLC purity: 100%. MS m/z 213 (M+H)+. *Reported in WO 00/76984, Example 169, Step 1.

Workup

  1. filtrationfollowed by filtration and concentration of the filtrate
  2. customgave 7.3 g of the crude product as an orange liquid
  3. customPurification
  4. filtrationby filtration through silica

Sources & evidence

ORD record
ord-1eef2ea18e1b4735af52676452dd5988
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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