Hydrochloric Acid → HCID 53766925, compound

Participants

Reaction Steps

5.53 g of powdered potassium carbonate was added to a solution of 4.34 g of 1,2,3,4-tetrahydrocarbazole-3-carboxylic acid, as obtained in Example 49, in 100 ml of N,N-dimethylformamide. 3.76 g of benzyl bromide were added to the reaction mixture, which was then stirred for 1.5 hours at room temperature, after which the mixture was neutralized by the addition of a 0.5N aqueous solution of hydrochloric acid. The aqueous layer was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 150 g of silica gel with a 4:1 v/v mixture of hexane and ethyl acetate as the eluent, and recrystallized from ethyl acetate and hexane, to yield 6.04 g of the title compound, melting at 104°-105° C.

Provenance & Evidence