Water → HCID 22483528, compound

HRID 1291934Notes

Reaction equation

HRID 1291934 reaction equation
O.[O:2]=[C:3]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]([CH2:12][CH:13]([OH:15])[CH3:14])[CH:6]=[CH:5][C:4]1=2>COCCOCCOC.[Pd]>[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:12][CH:13]([OH:15])[CH3:14]

Participants

5

Reactant 2

HCID 962WaterHCID 19598479HCID 19598479, compound

Product 1

HCID 22483528HCID 22483528, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8150DiglymeSolvent2×

Procedure

10 g of 5% by weight palladium-on-charcoal, containing 50% of water, were added to a solution of 19.3 g of 4-oxo-4,5,6,7-tetrahydro-1-N-(β-hydroxypropyl)indole, obtained in the preceding stage, in 300 cm3 of diglyme. The temperature of the reaction mixture was brought to the reflux temperature of the diglyme for 5 hours, after removal of the water by azeotropic distillation. The catalyst was then filtered off on Celite and the diglyme was then evaporated. 17 g of crude product were obtained. After chromatography on silica gel (heptane/ethyl acetate=1/4), 15 g of a viscous product were obtained, which product crystallized on addition of 15 cm3 of dichloromethane.

Workup

  1. customafter removal of the water
  2. distillationby azeotropic distillation
  3. filtrationThe catalyst was then filtered off on Celite
  4. customthe diglyme was then evaporated
  5. custom17 g of crude product were obtained

Sources & evidence

ORD record
ord-fc6b26d682a24de59079c90dd1c468ee
Source dataset
uspto-grants-1998_05
Patent number
US05755829

Reaction notes

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