Water → 1-Methyl-4-(5-nitropyridin-2-yl)piperazine

HRID 2102770Notes

Reaction equation

HRID 2102770 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 27640661-Methyl-4-(5-nitropyridin-2-yl)piperazineYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 2-chloro-5-nitropyridine (3.16 g, 20.0 mmol), 1-methyl-piperazine (2.00 g, 2.00 mmol) and potassium carbonate (2.76 g, 20.0 mmol) in DMF is heated at 100° C. for 24 h, cooled, poured into water and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (SiO2, 2% ammonia in 10:90 ethanol:ethyl acetate as eluent) affords the title compound as an off-white solid, 4.0 g (90% yield), identified by NMR analysis.

Workup

  1. temperaturecooled
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined extracts are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue is purified by flash chromatography (SiO2, 2% ammonia in 10:90 ethanol:ethyl acetate as eluent)

Sources & evidence

ORD record
ord-865acf80d0ec48708832b59e0ef2da8d
Source dataset
uspto-grants-2009_08
Patent number
US07576087B2

Reaction notes

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