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

HRID 2236421Notes

Reaction equation

HRID 2236421 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>CO.[Pd]>[N:9]1([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:16][CH:15]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 7835411-(4-Nitrobenzyl)piperidine

Product 1

HCID 8461504-(Piperidin-1-ylmethyl)anilineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(4-Nitro-benzyl)-piperidine (0.089 g, 0.404 mmol) is dissolved in MeOH (5 mL), and to this solution is added 10% Pd/C (0.009 g, 0.404 mmol). The reaction mixture is stirred under an atmosphere of H2 for 18 h. The resulting mixture is filtered through celite, and the filtered catalyst is washed with excess EtOAc. The filtrate is concentrated under high vacuum to afford the product as a solid (0.076 g, 99%); 1H NMR (DMSO-d6) δ 1.29-1.40 (m, 2H), 1.40-1.51 (m, 4H), 2.17-2.30 (m, 4H), 3.18 (s, 2H), 4.88 (s, 2H), 6.46 (d, J=8.4 Hz, 2H), 6.87 (d, J=8.4 Hz, 2H); mass spectrum [(+) ESI], m/z 191 (M+H)+

Workup

  1. filtrationThe resulting mixture is filtered through celite
  2. washthe filtered catalyst is washed with excess EtOAc
  3. concentrationThe filtrate is concentrated under high vacuum

Sources & evidence

ORD record
ord-6e81439cb17041f48f9abe532753bae0
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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