1-(4-Nitrobenzyl)piperidine → 4-(Piperidin-1-ylmethyl)aniline
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- additionwas added to the mixture
- filtrationThe palladium was filtered off
- concentrationthe filtrate was concentrated
- customThe residue was recrystallized from hexane
Sources & evidence
- ORD record
- ord-503b4ff6a8fa4e7798c018ced35f5f00
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06172061B2
Reaction notes
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