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

HRID 68440Notes

Reaction equation

HRID 68440 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[N:10][C:11]([N+:14]([O-])=O)=[CH:12][CH:13]=2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[N:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

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

Product 1

HCID 223298335-(4-Methylpiperazin-1-yl)pyridin-2-amineYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl-4-(6-nitro-pyridin-3-yl)-piperazine (1.748 g, 7.865 mmol) was stirred in 30 mL methanol with 175 mg 10% palladium on carbon under an atmosphere of hydrogen gas for 5 hours. This was filtered and concentrated in vacuo to yield 5-(4-Methyl-piperazin-1-yl)-pyridin-2-ylamine (1.485 g, 7.724 mmol). MS (ESI) 193.1 (M+H)+.

Workup

  1. filtrationThis was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0140dc06316a462cbb2fde20d99d6cd8
Source dataset
uspto-grants-2014_09
Patent number
US08822457B2

Reaction notes

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