1-(4-Nitrobenzyl)piperidine → 4-(Piperidin-1-ylmethyl)aniline

HRID 565831

Reaction equation

HRID 565831 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 7835411-(4-Nitrobenzyl)piperidine

Product 1

HCID 8461504-(Piperidin-1-ylmethyl)anilineYield 18.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In ethanol (50 ml) was dissolved 1-(4-nitrobenzyl)piperidine (6.41 g), and 10% dried palladium on carbon (0.33 g) was added to the mixture. Under hydrogen atmosphere, the mixture was stirred at room temperature under atmospheric pressure for 24 hours. The palladium was filtered off, and the filtrate was concentrated. The residue was recrystallized from hexane to give 1-(4-aminobenzyl)piperidine (1.01 g) as pale yellow crystals.

Workup

  1. additionwas added to the mixture
  2. filtrationThe palladium was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-503b4ff6a8fa4e7798c018ced35f5f00
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Linked notes

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