2-Nitro-N-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)benzeneamine → N1-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)-1,2-benzenediamine

HRID 395707Notes

Reaction equation

HRID 395707 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([O:13][CH:14]([CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)=[O:12])([O-])=O>C(O)C.[Pd]>[N:18]1[CH:19]=[CH:20][C:15]([CH:14]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[O:13][C:11]([NH:10][C:5]2[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:12])=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 700319012-Nitro-N-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)benzeneamine

Product 1

HCID 86585755N1-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)-1,2-benzenediamineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-nitro-N-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)benzeneamine (7.55 g, 21.2 mmol) and 5% palladium-on-carbon (4.00 g) in ethanol (250 mL) was placed under an atmosphere of hydrogen (1 bar). After consumption of the starting material (16-20 h), the mixture was filtered through diatomaceous earth. Hot ethyl acetate was used to wash the filter cake. Concentration of the filtrate in vacuo yielded 6.58 g (96%) of the title compound.

Workup

  1. customAfter consumption of the starting material (16-20 h)
  2. filtrationthe mixture was filtered through diatomaceous earth
  3. washto wash the filter cake

Sources & evidence

ORD record
ord-e1e4d49299ce415f9d38e4f49ccbd147
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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