Piperazine → 3-Chloropyrazine-2-carbonitrile

HRID 639838Notes

Reaction equation

HRID 639838 reaction equation
[NH:1]1CCNCC1.[Cl:7][C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=1>C(#N)C.ClCCl>[Cl:7][C:8]1[C:13]([C:12]#[N:1])=[N:14][CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 2924653-Chloropyrazine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

Piperazine (1.5 mmol) and 2-chloro-3-nitro-pyridine (1 mmol) were dissolved in acetonitrile (3 mL) and stirred for 30 min at 85° C. The reaction mixture was diluted with dichloromethane and washed with water. The organic layer was isolated, washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The product was purified (SPE column chromatography, silica gel, 0-10% methanol in ethyl acetate).

Workup

  1. washwashed with water
  2. customThe organic layer was isolated
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe product was purified (SPE column chromatography, silica gel, 0-10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-abf29ac5635e4fe49e889b36bc4b1da9
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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