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

HRID 1837162Notes

Reaction equation

HRID 1837162 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-315bae13d32246bcad8afe72531d8be9
Source dataset
uspto-grants-2004_08
Patent number
US06780878B2

Reaction notes

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