Triethylamine → 2,6-dihydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-benzamide

Participants

Reaction Conditions

Reaction Steps

Serotonin hydrochloride (430 mg, 2 mmol) and 2,6-dihydroxybenzoic acid (312 mg, 2 mmol) were dissolved in N,N-dimethylformamide (25 ml), and the solution temperature was maintained at 0° C. To this solution were added triethylamine (310 μl, 2.1 mmol), 1-hydroxybenzotriazole hydrate (HOBt H2O, 346 mg, 2.1 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI HCl, 429 mg, 2.1 mmol), the solution temperature was gradually warmed from 0° C. to room temperature, and the mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure, water (20 ml) was added to the residue, and the mixture was extracted twice with ethyl acetate (20 ml). The ethyl acetate layer was washed twice with 5% aqueous citric acid solution (5 ml), once with saturated brine (5 ml), twice with 5% aqueous sodium hydrogen carbonate solution (5 ml), and once with saturated brine (5 ml), and dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure, purified by preparative thin-layer chromatography (PTLC, eluent: ethyl acetate:hexane=3:1) to give 2,6-dihydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-benzamide (93 mg, yield 14.9%) as a powder.

Provenance & Evidence