Potassium Carbonate → 3-Methyl-1-(5-nitropyridin-2-yl)piperazine

HRID 2251804Notes

Reaction equation

HRID 2251804 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=1.[CH3:17][CH:18]1[CH2:23][NH:22][CH2:21][CH2:20][NH:19]1>CN(C)C=O>[CH3:17][CH:18]1[NH:19][CH2:20][CH2:21][N:22]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=2)[CH2:23]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660572-MethylpiperazineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 441197523-Methyl-1-(5-nitropyridin-2-yl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

872 mg (6.31 mmol) of potassium carbonate were added to a solution of 500 mg (3.15 mmol) of 2-chloro-5-nitropyridine in 7 ml of dimethylformamide. After that, a solution of 350 mg (3.32 mmol) of 2-methylpiperazine in 3 ml of dimethylformamide was slowly added dropwise to the reaction mixture while cooling with ice (exothermic reaction). The reaction mixture was stirred for 1 hour while cooling with ice and then stirred overnight at room temperature. After the solvent had been evaporated to dryness, the residue was taken up in water and this mixture was extracted three times with diethyl ether. The combined organic phases were dried over sodium sulfate, filtered and evaporated to dryness, with 3-methyl-1-(5-nitropyridin-2-yl)piperazine (Yield: 650 mg, 89% of theory) being obtained.

Workup

  1. temperaturewhile cooling with ice (exothermic reaction)
  2. temperaturewhile cooling with ice
  3. stirringstirred overnight at room temperature
  4. customAfter the solvent had been evaporated to dryness
  5. extractionthis mixture was extracted three times with diethyl ether
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness, with 3-methyl-1-(5-nitropyridin-2-yl)piperazine (Yield: 650 mg, 89% of theory)
  9. custombeing obtained

Sources & evidence

ORD record
ord-0f1fa8de6f20493d96dd5ba2104e3101
Source dataset
uspto-grants-2008_01
Patent number
US07320979B2

Reaction notes

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