Water → HCID 22483528, compound

HRID 362674Notes

Reaction equation

HRID 362674 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>[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: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 palladium on carbon at 5% by weight and containing 50% 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 medium was raised to the reflux temperature of diglyme for 5 hours, after removing the water by azeotropy. The catalyst was then filtered off on celite and then the diglyme was evaporated off. 17 g of crude product were obtained. After chromatography on silica gel (heptane/ethyl acetate=1/4), 15 g of viscous product were obtained, which product was crystallized by the addition of 15 cm3 of dichloromethane.

Workup

  1. customafter removing the water by azeotropy
  2. filtrationThe catalyst was then filtered off on celite
  3. customthe diglyme was evaporated off
  4. custom17 g of crude product were obtained

Sources & evidence

ORD record
ord-d2d6072420294d2fa4086aa51f09f08f
Source dataset
uspto-grants-1999_02
Patent number
US05869692

Reaction notes

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