Tryptamine → HCID 53654476, compound

Participants

Reaction Steps

2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]-ethylamine hydrochloride salt (1 g) was suspended in dry methylene chloride (25 mL) and dry triethylamine (0.806 mL) was added and stirred for 5 minutes at room temperature. [2-(tert-butoxycarbonyloxyimino)phenylacetronitrile] (890 mg) was added in small portions over 5 minutes to the tryptamine and the reaction mixture left to stir overnight at room temperature. The reaction was partitioned between methylene chloride and 5% citric acid. The methylene chloride layer was separated and washed with brine and dried over anhydrous sodium sulfate powder. The extract was filtered and evaporated to dryness. The product was isolated by column chromatography using silica gel and an eluant of ethyl acetate and hexanes (35:65 v/v). The yield of the title compound was 1 g.

Provenance & Evidence