2-Nitro-n-[1-(4-pyridyl)piperidin-4-ylmethyl]aniline → N1-[1-(4-pyridyl)piperidin-4-ylmethyl)-1,2-benzenediamine

HRID 49837Notes

Reaction equation

HRID 49837 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[NH:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)([O-])=O>[Pd].C(O)C>[N:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][CH:8]([CH2:7][NH:6][C:5]3[C:4]([NH2:1])=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:9][CH2:10]2)=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 121506972-Nitro-n-[1-(4-pyridyl)piperidin-4-ylmethyl]aniline

Product 1

HCID 12150698N1-[1-(4-pyridyl)piperidin-4-ylmethyl)-1,2-benzenediamineYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-nitro-N-[1-(4-pyridyl)piperidin-4-yl-methyl]aniline (235 mg, 0.75 mmol) and 10% palladium on carbon (200 mg) in ethanol (4 mL) was placed under an atmosphere of hydrogen gas. After 1 h, the mixture was filtered through diatomaceous earth. The filtrate was concentrated yielding 212 mg of the title compound, which was used without further purification.

Workup

  1. filtrationthe mixture was filtered through diatomaceous earth
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5de4cb95018947a98843320b25c3ae62
Source dataset
uspto-grants-2004_03
Patent number
US06710057B2

Reaction notes

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