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

HRID 70760Notes

Reaction equation

HRID 70760 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>C(OCC)(=O)C.C(O)C.[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

5

Reactant 1

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

Product 1

HCID 223298335-(4-Methylpiperazin-1-yl)pyridin-2-amineYield 74.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-methyl-4-(6-nitro-3-pyridyl)piperazine 3.4 g in ethyl acetate (100 mL) and ethanol (100 mL) was added 10% Pd/c (400 mg) and then contents stirred under hydrogen (10 psi) overnight. After filtration through CELITE™, the solvents were evaporated and the crude product was purified over silica gel using DCM/7N Ammonia in MeOH (0-5%) to afford 5-(4-methylpiperazin-1-yl)pyridin-2-amine (2.2 g). 1HNMR (d6-DMSO) 7.56 (1H, d, J=3 Hz), 7.13 (1H, m), 6.36 (1H, d, J=8.8 Hz), 5.33 (brs, 2H), 2.88 (m, 4H), 2.47 (m, 4H), 2.16 (s, 3H).

Workup

  1. filtrationAfter filtration through CELITE™
  2. customthe solvents were evaporated
  3. customthe crude product was purified over silica gel

Sources & evidence

ORD record
ord-576cde6f8b8042c8a611a66c5bb82e3f
Source dataset
uspto-grants-2014_09
Patent number
US08822683B2

Reaction notes

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