1-Isopropyl-4-(2-methyl-6-nitro-pyridin-3-yl)-piperazine → 5-(4-Isopropyl-piperazin-1-yl)-6-methyl-pyridin-2-ylamine

HRID 2264353Notes

Reaction equation

HRID 2264353 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[C:11]([CH3:19])=[N:12][C:13]([N+:16]([O-])=O)=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]>CO.CC(=O)OCC.[Pd]>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[N:12][C:11]=2[CH3:19])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 674271951-Isopropyl-4-(2-methyl-6-nitro-pyridin-3-yl)-piperazine

Product 1

HCID 674269485-(4-Isopropyl-piperazin-1-yl)-6-methyl-pyridin-2-ylamineYield 99.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Stir 1-isopropyl-4-(2-methyl-6-nitro-pyridin-3-yl)-piperazine (2.52 g) and palladium over carbon 10% (600 mg) in methanol (38 mL) and EA (38 mL) under H2 (balloon) overnight. Filter over a celite pad and remove the solvent under vacuum. Purify by silica gel column chromatography eluting with DCM/methanol (0-10%) to afford 2.23 g of the title compound. MS (ES+): m/z=143 (M+H)+.

Workup

  1. filtrationFilter over a celite pad
  2. customremove the solvent under vacuum
  3. customPurify by silica gel column chromatography
  4. washeluting with DCM/methanol (0-10%)

Sources & evidence

ORD record
ord-3c233a23998941b6bafcb62fb49edcd9
Source dataset
uspto-grants-2010_12
Patent number
US07855211B2

Reaction notes

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