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

HRID 2195047Notes

Reaction equation

HRID 2195047 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>CC(N(C)C)=O>[CH3:8][C:7]1[C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:3][CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 896482-Chloro-3-methyl-5-nitropyridine

Product 1

HCID 566870601-(3-Methyl-5-nitropyridin-2-yl)piperazine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1-(3-Methyl-5-nitro-pyridin-2-yl)-piperazine is prepared by heating a solution of 1 g of 2-chloro-3-methyl-5-nitro-pyridine (Maybridge Chemical Company Ltd.) and piperazine (5 g) in DMA at 110° C. for 16 h. Partition between EtOAc and water and wash the organic layer with water (2×). Dry the organic layer with Na2SO4 and concentrate to give crude product. Purify via flash chromatography eluting with MeOH:DCM:NH4OH (9:90:1) to give the title compound.

Workup

  1. custom1-(3-Methyl-5-nitro-pyridin-2-yl)-piperazine is prepared
  2. customPartition between EtOAc and water
  3. washwash the organic layer with water (2×)
  4. dry with materialDry the organic layer with Na2SO4
  5. concentrationconcentrate
  6. customto give crude product
  7. customPurify via flash chromatography
  8. washeluting with MeOH:DCM:NH4OH (9:90:1)

Sources & evidence

ORD record
ord-30fed76a861649a194bb4650a60bb03a
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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