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

HRID 1837682Notes

Reaction equation

HRID 1837682 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]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:1]2[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]2)=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4207714-PiperidinemethanolHCID 149329453-(Chloromethyl)-2-methoxypyridine

Product 1

HCID 226786771-[(2-Methoxy-3-pyridyl)methyl]-4-piperidinemethanolYield 82.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g of 4-piperidinemethanol, 13 g of 3-(chloromethyl)-2-methoxypyridine and 24 g of potassium carbonate were suspended in 80 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 12 hours. Water was added to the reaction solution, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then the layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, to give 16.1 g of the title compound as a pale brown oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialthe layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f31665bf31fb4233bcc246747330e02b
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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