Dichloromethane → 1-(2-Methoxy-4-propoxyphenyl)piperidin-4-one

HRID 1470744Notes

Reaction equation

HRID 1470744 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH3:13])[CH:7]=[CH:6][C:4]=1[NH2:5].[I-].C[N+]1(CC2C=CC=CC=2)[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1.C(Cl)Cl>CCO.O>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH3:13])[CH:7]=[CH:6][C:4]=1[N:5]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 110780641-Benzyl-1-methyl-4-oxopiperidinium iodideHCID 636778052-Methoxy-4-propoxyaniline

Product 1

HCID 679714051-(2-Methoxy-4-propoxyphenyl)piperidin-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1.20 g (6.62 mmol) 2-methoxy-4-propoxyaniline (Example XXXI) in 8.5 mL EtOH and 1.8 mL water are stirred under reflux. During 30 min 2.19 g (6.62 mmol) N-methyl-N-benzyl-4-oxopiperidinium iodide (Org. Lett. 1999, 1, 1261-1262) are added by several portions. Stirring under reflux is continued for 1 h. Then the reaction mixture is cooled down to rt before water and DCM are added. The layers are separated and the org. layer is dried with MgSO4, filtered and the solvent is removed in vacuo. The resulting residue is purified by column chromatography (silica gel, PE/EtOAc 8/2).

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux
  3. additionare added
  4. customThe layers are separated
  5. dry with materiallayer is dried with MgSO4
  6. filtrationfiltered
  7. customthe solvent is removed in vacuo
  8. customThe resulting residue is purified by column chromatography (silica gel, PE/EtOAc 8/2)

Sources & evidence

ORD record
ord-de287a234e7a4c9bb183c95535ef6966
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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