2-[1-(4-Pyridyl)piperidin-4-ylmethylaminocarbonyl]amino-nitrobenzene → N1-[1-(4-Pyridyl)piperidin-4-ylmethylaminocarbonyl)-1,2-benzenediamine

HRID 2301849Notes

Reaction equation

HRID 2301849 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:24]([O-])=O)=[O:16])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][NH:14][C:15]([NH:17][C:18]3[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:16])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 181744692-[1-(4-Pyridyl)piperidin-4-ylmethylaminocarbonyl]amino-nitrobenzene

Product 1

HCID 10496290N1-[1-(4-Pyridyl)piperidin-4-ylmethylaminocarbonyl)-1,2-benzenediamineYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-[1-(4-pyridyl)piperidin-4-ylmethylaminocarbonyl]amino-nitrobenzene (1.02 g, 2.87 mmol) in ethanol was hydrogenated at atmospheric pressure over 5% palladium-on-carbon. After completion (16-20 h), the mixture was filtered through diatomaceous earth, using hot ethyl acetate to wash the filter cake. Concentration of the filtrate in vacuo yielded 930 mg (99%) of the title compound.

Workup

  1. filtrationAfter completion (16-20 h), the mixture was filtered through diatomaceous earth
  2. washto wash the filter cake

Sources & evidence

ORD record
ord-e74dc2178cea419a8f0d7dc62e13d82e
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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