Piperazine → HCID 22560452, compound

HRID 2403573Notes

Reaction equation

HRID 2403573 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[N:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:16][C:14]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[N:15]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 5204002-Chloro-6-methylpyridine-3-carbonitrile

Product 1

HCID 22560452HCID 22560452, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Piperazine (1.13 g) and 2-chloro-6-methylnicotinonitrile (500 mg) were dissolved in DMF (15 ml), and K2CO3 (1.36 g) was added thereto, followed by stirring at 60° C. overnight. The reaction mixture was concentrated under reduced pressure, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain 6-methyl-2-piperazin-1-ylnicotinonitrile (628 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogen carbonate solution was added
  3. extractionfollowed by extraction with CHCl3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-d1ce4ddeed0b47fd8e9b02e3df501a21
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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