Ammonium Hydroxide → HCID 20299751, compound

Participants

Reaction Conditions

Reaction Steps

The product of Step C was empasted with 50 ml of water and an excess of ammonium hydroxide was added thereto. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness. The 11.55 g of orange oil residue were added to 45 g of pyridine and the mixture was refluxed at 220° C. under an inert atmosphere for 135 minutes. The mixture was cooled to 20° C. and was made alkaline with ammonium hydroxide. The mixture was then extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness. The 12.8 g of reddish oil residue were dissolved in 60 ml of isopropanol and an excess of ethyl acetate saturated with hydrogen chloride was added thereto. The ethyl acetate was distilled and crystallization was induced after which the mixture was held overnight in a refrigerator. The mixture was vacuum filtered and the recovered product was washed with isopropanol and dried to obtain 9.3 g of 3-[2-({2-(1H-indol-3-yl)-ethyl}-propylamino)-ethyl]-phenol hydrochloride in the form of a clear beige solid melting at 192° C., then 197° C. Crystallization of the product from ethanol yielded a product melting at 198° C.

Provenance & Evidence