1-(2-Methoxy-4-nitrophenyl)piperidine → 3-Methoxy-4-(piperidin-1-yl)aniline

HRID 1993518Notes

Reaction equation

HRID 1993518 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(O)C.C1COCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 28254311-(2-Methoxy-4-nitrophenyl)piperidine

Product 1

HCID 152564913-Methoxy-4-(piperidin-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

1-(2-Methoxy-4-nitro-phenyl)-piperidine (Stage 85.2; 4.0 g, 17 mmol) in ethanol/THF 5:1 (90 ml) is hydrogenated in the presence of Pd/C 10 % (“Engelhard 4505”; 0.4 g). Then the catalyst is filtered off and the filtrate is concentrated yielding the title compound: 1H-NMR (DMSO-d6): 6.58 (d, 1H), 6.19 (d, 1H), 6.04 (dd, 1H), 4.66 (s, H2N), 3.65 (s, H3CO), 2.70 (m, 4H), 1.56 (m, 4H), 1.43 (m, 2H).

Workup

  1. filtrationThen the catalyst is filtered off
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-1706530928164d84b556ccb7e99023d6
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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