1-Methyl-4-(4-nitrophenyl)piperidine → 4-(1-Methylpiperidin-4-yl)aniline

HRID 1517653Notes

Reaction equation

HRID 1517653 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[H][H]>C(O)C.C1COCC1.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 219595311-Methyl-4-(4-nitrophenyl)piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 219595294-(1-Methylpiperidin-4-yl)aniline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.3 g (19.5 mmol) 1-methyl-4-(4-nitro-phenyl)-piperidine are dissolved in a mixture of 60 ml of ethanol and 60 ml THF, combined with 2 g palladium/charcoal (10%) and hydrogenated at 1 bar hydrogen. Then the reaction mixture is suction filtered and the filtrate is concentrated by evaporation. Yield: 3.5 g

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-4e59960bccd64f0c931cc4f38cfff7d2
Source dataset
uspto-grants-2012_07
Patent number
US08232286B2

Reaction notes

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