Water → HCID 22678633, compound

HRID 1837684Notes

Reaction equation

HRID 1837684 reaction equation
[Br-].[CH2:2]1[O:30][C:29]2[C:4](=[C:5]([CH:26]=[CH:27][CH:28]=2)[CH2:6][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:3]1.[CH3:31][C:32]([CH3:35])([O-])[CH3:33].[K+].O.[H][H].[CH3:40][N:41]([CH3:44])[CH:42]=O>C(O)C.[C].[Pd]>[CH2:40]([N:41]1[CH2:44][CH2:33][CH:32]([CH2:35][CH2:6][C:5]2[CH:26]=[CH:27][CH:28]=[C:29]3[O:30][CH2:2][O:3][C:4]=23)[CH2:31][CH2:42]1)[C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:5]=1

Participants

8

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 22678559HCID 22678559, compoundHCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 22678633HCID 22678633, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

20.3 g of 4-(1-benzyl)piperidinecarboxaldehyde and 48.0 g of (2,3-methylenedioxybenzyl)triphenylphosphonium bromide and 12.0 g of potassium tert-butoxide were suspended in 200 ml of N,N-dimethylformamide, 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 and separated by NH form silica gel column chromatography (ethyl acetate:hexane=1:4). The resulting product and 2.03 g of 10% palladium-carbon powder (water-containing product) were suspended in 200 ml of ethanol. After replacing the atmosphere of a container with hydrogen, the mixture was stirred at room temperature under ordinary atmosphere for two hours. The reaction solution was filtered, and the filtrate was evaporated, to give 20.3 g of the title compound as a colorless 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
  6. customseparated by NH
  7. customform silica gel column chromatography (ethyl acetate:hexane=1:4)
  8. stirringthe mixture was stirred at room temperature under ordinary atmosphere for two hours
  9. filtrationThe reaction solution was filtered
  10. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-3114c3d0058b4d109a77c97ca0f7bbba
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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