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

HRID 1366288Notes

Reaction equation

HRID 1366288 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.[H][H]>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

5

Reactant 2

HCID 574161554-(3-Methoxy-4-nitrophenoxy)-1-methylpiperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 552341692-Methoxy-4-[(1-methylpiperidin-4-yl)oxy]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(3-Methoxy-4-nitro-phenoxy)-1-methyl-piperidine (3.0 g, 11.3 mmol) in ethanol (50 mL), 5% palladium on carbon (300 mg) is added under a nitrogen atmosphere. The reaction vessel is fitted with a balloon adapter and charged with hydrogen and evacuated three times until the reaction is under a hydrogen atmosphere. The reaction is allowed to stir overnight. The reaction mixture is filtered through a pad of Celite and washed with methanol. The filtrate is concentrated in vacuo to afford 2-Methoxy-4-(1-methyl-piperidin-4-yloxy)-phenylamine in quantitative yield (2.7 g).

Workup

  1. customThe reaction vessel is fitted with a balloon adapter
  2. customevacuated three times until the reaction
  3. filtrationThe reaction mixture is filtered through a pad of Celite
  4. washwashed with methanol
  5. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-0d9dc8ba1234465bbf917f66bfde1a61
Source dataset
uspto-grants-2011_02
Patent number
US07893074B2

Reaction notes

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