4-(3-Methoxy-4-nitrophenoxy)-1-methylpiperidine → 2-Methoxy-4-[(1-methylpiperidin-4-yl)oxy]aniline

HRID 2234364Notes

Reaction equation

HRID 2234364 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[O:6][CH:7]1[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)[CH:14]=[CH:15][C:16]=1[NH2:17]

Participants

4

Reactant 1

HCID 574161554-(3-Methoxy-4-nitrophenoxy)-1-methylpiperidine2×

Product 1

HCID 552341692-Methoxy-4-[(1-methylpiperidin-4-yl)oxy]anilineYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-(3-methoxy-4-nitro-phenoxy)-1-methyl-piperidine (Intermediate 44; 12.86 g, 48.34 mmol) in ethanol (250 mL) under nitrogen was added in one portion the Pd/C catalyst (10%, 1.29 g). The resulting mixture was evacuated and backfilled with nitrogen 4× before hydrogen gas was introduced via a balloon. The reaction mixture was stirred at room temperature for 18 hrs. The catalyst was removed by filtration through celite and the filtrate concentrated under reduced pressure to give a light red oil (11.1 g, 47.0 mmol, 97%).

Workup

  1. customThe resulting mixture was evacuated
  2. additionwas introduced via a balloon
  3. customThe catalyst was removed by filtration through celite
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-66c7bc436e4343aba69fdfd74d1d8d3f
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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