1-Methyl-4-(3-nitropyridin-2-yl)piperazine → Piperazine, 1-(3-amino-2-pyridyl)-4-methyl-

HRID 2367684Notes

Reaction equation

HRID 2367684 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 27645231-Methyl-4-(3-nitropyridin-2-yl)piperazine

Product 1

HCID 199808Piperazine, 1-(3-amino-2-pyridyl)-4-methyl-Yield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirring solution of 1-methyl-4-(3-nitro-pyridin-2-yl)-piperazine (LXXXIII) (1.30 g, 5.85 mmol) in MeOH (15 mL) was added 10% Pd/C. The solution was purged with hydrogen. The solution was stirred at room temperature for 16 h under hydrogen. The solution was filtered through a pad of Celite and concentrated to a residue under vacuum. The residue was purified by column chromatography (100% CHCl3→2:98 MeOH[7N NH3]:CHCl3) to afford 2-(4-methylpiperazin-1-yl)pyridin-3-amine (LXXXIV) (0.466 g, 2.42 mmol, 52% yield) as a tan solid. ESIMS found for C10H16N4 m/z 192.4 (M+H).

Workup

  1. customThe solution was purged with hydrogen
  2. filtrationThe solution was filtered through a pad of Celite
  3. concentrationconcentrated to a residue under vacuum
  4. customThe residue was purified by column chromatography (100% CHCl3→2:98 MeOH[7N NH3]:CHCl3)

Sources & evidence

ORD record
ord-7db95214ac2e43a4b454dc639ab54245
Source dataset
uspto-grants-2014_04
Patent number
US08697887B2

Reaction notes

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