Water → 1-[(2-Methoxy-3-pyridyl)methyl]-4-piperidone

HRID 1837696Notes

Reaction equation

HRID 1837696 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.Cl[CH2:10][C:11]1[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:18][O:17][C:12]1[C:11]([CH2:10][N:2]2[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]2)=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30848514-Piperidone hydrochlorideHCID 149329453-(Chloromethyl)-2-methoxypyridine

Product 1

HCID 226783211-[(2-Methoxy-3-pyridyl)methyl]-4-piperidoneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.0 g of 4-piperidone hydrochloride, 4.1 g of 3-(chloromethyl)-2-methoxypyridine and 12.6 g of potassium carbonate were suspended in 26 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 15 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (ethyl acetate), to give 5.5 g of the title compound as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-db44b3c7d5294f7faa0042b0398aef6d
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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