Methanol → HCID 23565315, compound

HRID 1059336Notes

Reaction equation

HRID 1059336 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:16][CH:17]=[O:18])([CH:14]=[CH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH2:42]([O:44]CC)C>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:16][C:17]([O:44][CH3:42])=[O:18])([CH:14]=[CH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 2724130Cornforth reagentHCID 23564093HCID 23564093, compound

Product 1

HCID 23565315HCID 23565315, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.486 g of (1-benzyl-4-vinylpiperidin-4-yl)acetaldehyde in N,N-dimethylformamide (10 ml) were added 0.48 g of methanol and 4.50 g of pyridinium dichromate and the resulting mixture was stirred at room temperature for 20 hours. After adding 100 ml of diethyl ether, the reaction mixture was filtered through celite. After concentrating under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.321 g of the title compound as a colorless oily substance.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationAfter concentrating under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-99261459752045289ccc92ef62728b2b
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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