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

HRID 1387764Notes

Reaction equation

HRID 1387764 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-1e282cdf0424491f98045e5eb2d0dd0e
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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