Aluminum(III) Chloride → HCID 22139220, compound

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (0.93 g, 24.5 mmol) in anhydrous tetrahydrofurane (15 ml), aluminum trichloride (3.5 g, 24.5 mmol) was added portionwise at 0° C. for 30 min and then 6-[N-(2-methoxyethyl)carbamoyl]indole (1 g, 4.5 mmol) was added portionwise at 0° C. for 1 h. After stirring overnight at room temperature, the reaction mixture was quenched with 20% NaOH while cooling in ice water. The precipitate was filtered and washed with dichloromethane and the solvent evaporated after dried over anhydrous sodium sulfate. The residue was chromatographed on silica gel (eluent, dichloromethane:methanol, 9:1) and then the product was precipitated with hexane to give 0.3 g (32%) of 6-[(2-methoxyethyl)aminomethyl]indole.

Provenance & Evidence