Tetrahydrofuran → HCID 25103524, compound

Participants

Reaction Steps

1-(3′-Hydroxybenzenesulfonyl) indole (0.602 mmol, 0.163 grams) (obtained from preparation 1) was taken in 50 mL two neck round bottom flask and added tetrahydrofuran (7 mL). To the above mixture potassium carbonate (1.24 mmol, 0.171 grams) was added and stirred for a period of 15-20 minutes. The free base generated from 2-dimethylaminoethyl chloride hydrochloride (2.48 mmol, 0.358 grams), by dissolving it in a solution of 3 mL 40% aqueous sodium hydroxide, diluted with 5 mL water and extracting free base with toluene (3 mL) was directly charged to reaction mixture. Reaction mixture was kept on reflux temperature and the progress was monitored. After completion of reaction, the reaction mass was cooled to room temperature, poured onto 25 mL of water and extracted the product with ethyl acetate (10 mL×4). Combined organic extracts were dried over sodium sulfate and the volatiles were removed under the reduced pressure to obtain 0.214 grams crude compound. The compound was purified by column chromatography using silica gel (100-200 mesh), the eluents being ethyl acetate and n-hexane (2:3) to obtain pure compound.

Provenance & Evidence