Water → HCID 19598480, compound

HRID 724748Notes

Reaction equation

HRID 724748 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>[Pd].COCCOCCOC>[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 palladium on carbon at 5% by weight and 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 medium was raised to the reflux temperature of diglyme and the water was distilled off by azeotropy. After 23 hours of reaction, the catalyst was filtered off on celite and then the diglyme was evaporated off 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 whose analysis by 1H and 13C nuclear magnetic resonance was in conformity with the expected product.

Workup

  1. distillationthe water was distilled off by azeotropy
  2. customAfter 23 hours of reaction
  3. filtrationthe catalyst was filtered off on celite
  4. customthe diglyme was evaporated off under vacuum
  5. customThe crude product obtained
  6. customwas chromatographed on silica gel (ethyl acetate/heptane=9/1 )

Sources & evidence

ORD record
ord-83f4148a9f934653a89699490bbd6bf9
Source dataset
uspto-grants-1998_01
Patent number
US05704948

Reaction notes

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