Water → HCID 22483528, compound

Participants

Reaction Steps

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.

Provenance & Evidence