P-Anisidine → 1-(4-Methoxyphenyl)piperidin-4-one

HRID 1363379Notes

Reaction equation

HRID 1363379 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.[Br-].C([N+]1(C)[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1)C1C=CC=CC=1>C(O)C.O>[CH3:7][O:8][C:9]1[CH:15]=[CH:14][C:12]([N:13]2[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7732P-AnisidineHCID 11430Potassium CarbonateHCID 10802960Piperidinium, 1-methyl-4-oxo-1-(phenylmethyl)-, bromide

Product 1

HCID 212605551-(4-Methoxyphenyl)piperidin-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Anhydrous potassium carbonate was added to a solution of 4-methoxyaniline (1.2 g, 9.8 mmol) in ethanol (10 mL) followed by a dropwise addition of a solution of compound of example 116 (2.77 g, 9.8 mmol) in water (3.0 mL). The reaction mixture was heated at 100° C. for 1 h., allowed to cool to room temperature, poured into ice water (100 mL) and extracted using EtOAc (3×50 mL). The organic extract was washed with water, dried (anhydrous Na2SO4) and concentrated to get the title compound.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried (anhydrous Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-105656c42b89430897ae896cee94d43d
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

Loading…