Ethanol → 3-Methoxy-4-(1-methylpiperidin-4-yl)aniline

HRID 869256Notes

Reaction equation

HRID 869256 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:16]C(=O)OCC2C=CC=CC=2)[CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1.C(O)C>[Pd].C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1)[NH2:16]

Participants

5

Reactant 2

HCID 702EthanolHCID 86662055Benzyl [3-methoxy-4-(1-methylpiperidin-4-yl)phenyl]carbamate

Product 1

HCID 574160883-Methoxy-4-(1-methylpiperidin-4-yl)anilineYield 102.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of benzyl [3-methoxy-4-(1-methylpiperidin-4-yl)phenyl]carbamate (Preparation Example 464) (1.26 g), ethanol (20 mL) and THF (10 mL), 5% palladium on carbon (0.38 g) was added and stirred overnight at room temperature under a hydrogen atmosphere at normal pressure. After filtration through celite, the filtrate was distilled off under reduced pressure to give 3-methoxy-4-(1-methylpiperidin-4-yl)aniline (0.80 g) as a light pink solid.

Workup

  1. additionwas added
  2. filtrationAfter filtration through celite
  3. distillationthe filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-15f27d3dfc67400ca67ec4d94ed292ce
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

Loading…