Water → HCID 19598480, compound

HRID 1291938Notes

Reaction equation

HRID 1291938 reaction equation
O.[O:2]=[C:3]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]([CH2:12][CH:13]([OH:16])[CH2:14][OH:15])[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:16])[CH2:14][OH:15]

Participants

5

Reactant 2

HCID 962WaterHCID 19598478HCID 19598478, compound

Product 1

HCID 19598480HCID 19598480, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8150DiglymeSolvent2×

Procedure

3.8 g of 5% by weight palladium-on-charcoal, containing 50% of water, were introduced into a solution of 9.4 g of 4-oxo-4,5,6,7-tetrahydro-1-N-(β,γ-dihydroxypropyl)indole, obtained in the preceding stage, in 50 cm3 of diglyme. The temperature of the reaction mixture was brought to the reflux temperature of the diglyme and the water was azeotropically distilled. After reacting for 23 hours, the catalyst was filtered off on Celite and the diglyme was then evaporated under vacuum. The crude product obtained was chromatographed on silica gel (ethyl acetate/heptane=9/1). 4.2 g of 4-hydroxy-1-N-(β,γ-dihydroxypropyl)indole were obtained in the form of a very viscous oil.

Workup

  1. distillationthe water was azeotropically distilled
  2. filtrationthe catalyst was filtered off on Celite
  3. customthe diglyme was then evaporated under vacuum
  4. customThe crude product obtained
  5. customwas chromatographed on silica gel (ethyl acetate/heptane=9/1)

Sources & evidence

ORD record
ord-902ac1fe3d1e4eaab0dad9897046d4ed
Source dataset
uspto-grants-1998_05
Patent number
US05755829

Reaction notes

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