2-Nitro-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline → N1-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)-1,2-benzenediamine

HRID 427557Notes

Reaction equation

HRID 427557 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([O:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18](C2C=CN=CC=2)[CH2:17][CH2:16]1)=[O:12])([O-])=O>C(O)C.[Pd]>[N:18]1[CH:19]=[CH:20][C:15]([CH:14]([CH:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]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 181746182-Nitro-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline

Product 1

HCID 86585755N1-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)-1,2-benzenediamineYield 190.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-nitro-N-[1-(4-pyridyl)piperidin-4-yl-methoxycarbonyl)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-5e40831a1e5043f883251c4a96f5e55a
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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