Hexane → 2-Chloro-3-(4-isopropylpiperazin-1-yl)pyrazine

HRID 1295714Notes

Reaction equation

HRID 1295714 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH:9]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].CCCCCC>C(#N)C>[Cl:8][C:7]1[C:2]([N:15]2[CH2:16][CH2:17][N:12]([CH:9]([CH3:11])[CH3:10])[CH2:13][CH2:14]2)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 780131-IsopropylpiperazineHCID 785752,3-Dichloropyrazine

Product 1

HCID 616994222-Chloro-3-(4-isopropylpiperazin-1-yl)pyrazineYield 79.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture 2,3-dichloro-pyrazine (5.0 g, 34 mmol), 1-isopropylpiperazine (6.5 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 9.5 g of crude material as an orange liquid. Purification by filtration through silica using heptane/EtOAc (3:1), followed by EtOAc/acetone (1:1), provided 6.5 g (79%) of the title compound as a yellow oil which solidified upon cooling. HPLC purity: 98%. MS m/z 241 (M+H)+. HRMS m/z calcd for C11H17ClN4 (M)+ 240.1142, found 240.1138.

Workup

  1. filtrationfollowed by filtration and concentration of the filtrate
  2. customgave 9.5 g of crude material as an orange liquid
  3. customPurification
  4. filtrationby filtration through silica

Sources & evidence

ORD record
ord-d5b90ca050ea4e95b2eb25b9f353cd8e
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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