1-Methylpiperazine → 1-Methyl-4-(6-nitropyridin-3-yl)piperazine

HRID 2189270Notes

Reaction equation

HRID 2189270 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>O>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:2]2[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 517114841-Methyl-4-(6-nitropyridin-3-yl)piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-2-nitropyridine (500 mg, 2.46 mmol) and 1-methylpiperazine (1 mL) is heated at 80° C. for 2 hour. Then water is added. The aqueous layer is extracted with EtOAc, and the organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=0.7:99.3 to 6:93) to give 520 mg of the title compound as yellow solid.

Workup

  1. extractionThe aqueous layer is extracted with EtOAc
  2. washthe organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=0.7:99.3 to 6:93)

Sources & evidence

ORD record
ord-a219be032f7241e687aa82ad7ddc8104
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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