Water → 1-[(2-Methoxy-3-pyridinyl)methyl]-4-piperidinecarboxaldehyde

HRID 1837683Notes

Reaction equation

HRID 1837683 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.O>CS(C)=O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([CH:16]=[O:17])[CH2:14][CH2:15]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 226786771-[(2-Methoxy-3-pyridyl)methyl]-4-piperidinemethanol

Product 1

HCID 226784071-[(2-Methoxy-3-pyridinyl)methyl]-4-piperidinecarboxaldehydeYield 68.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

16.1 g of 1-[(2-methoxy-3-pyridyl)methyl]-4-piperidinemethanol and 38 ml of triethylamine were suspended in 60 ml of dimethyl sulfoxide, a mixed solution of 21.7 g of a sulfur trioxide-pyridine complex and 100 ml of dimethyl sulfoxide was added dropwise thereto, and the mixture was stirred at room temperature for one hour. 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 10.9 g of the title compound as a pale 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-0338fe04f06843398eb7c5ed8d4d9ea5
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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