2-Nitro-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline → N2-[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl-1,2-benzenediamine

HRID 842381Notes

Reaction equation

HRID 842381 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[NH:6][C:7]([O:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:8])([O-])=O>C(O)C.[Pd]>[N:20]1[CH:21]=[CH:22][C:17]([N:14]2[CH2:13][CH2:12][CH:11]([CH2:10][O:9][C:7]([NH:6][C:5]3[C:4]([NH2:1])=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:8])[CH2:16][CH2:15]2)=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 181746182-Nitro-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline

Product 1

HCID 10829995N2-[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl-1,2-benzenediamineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-nitro-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline (7.55 g, 21.2 mmol) and 5% Pd/C (4.00 g) in ethanol was placed under an atmosphere of hydrogen (1 atm). After consumption of the starting material was indicated by tlc (16-20 h), the mixture was filtered through diamotaceous earth using hot ethyl acetate to wash the filter cake. Concentration of the filtrate yielded 6.58 g (96%) of the title compound.

Workup

  1. customAfter consumption of the starting material
  2. customwas indicated by tlc (16-20 h)
  3. filtrationthe mixture was filtered through diamotaceous earth
  4. washto wash the filter cake

Sources & evidence

ORD record
ord-df985a8a87264d12a6efe8d3ab7c5574
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

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