Water → HCID 22483528, compound

HRID 611784Notes

Reaction equation

HRID 611784 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-oxo4,5,6,7-tetrahydro-1-N-(β-hydroxy-propyl)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. After filtering, washing with petroleum ether and drying under vacuum and over phosphorus pentoxide, 10 g of 4-hydroxy-1-N-(β-hydroxypropyl)indole were recovered, the melting point of which was between 93 and 95° C.

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-0b614126baba4a59bf285b83819e0410
Source dataset
uspto-grants-1999_12
Patent number
US06002018

Reaction notes

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