1-Methyl-4-(5-nitropyridin-2-yl)piperazine → 6-(4-Methylpiperazin-1-yl)pyridin-3-amine

HRID 2236524Notes

Reaction equation

HRID 2236524 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 27640661-Methyl-4-(5-nitropyridin-2-yl)piperazine

Product 1

HCID 27633906-(4-Methylpiperazin-1-yl)pyridin-3-amineYield 104.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

An amount of 1 g (4.48 mmol) of 1-Methyl-4-(5-nitro-pyridin-2-yl)-piperazine is dissolved in methanol (50 mL), followed by a catalytic amount of 10% Pd/C. The mixture is hydrogenated at 35-40 psi for 3 hours, filtrated through celite followed by evaporation to give 900 mg (100% yield) of purple solid; mp 97-98° C. MS (ESI) m/z 193.1 (M+1)+.

Workup

  1. filtrationfiltrated through celite
  2. customfollowed by evaporation

Sources & evidence

ORD record
ord-ed8c7d9ac2184ac3901354ddfd7d627b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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