Pyridine → N-Acetylserotonin

Participants

Reaction Conditions

Reaction Steps

N-acetyl serotonin was synthesized as follows. 100 mg (0.47 mmol) serotonin hydrochloride and 10 mL of pyridine were mixed in a 100 mL round-bottomed flask, and the solution was cooled to 0° C. under argon. Acetic anhydride (2.84 g, 28.4 mmol) was added slowly over 1 hr. After stirring at 0° C. for 20 hr the reaction was terminated by removing the volatile reagents under high vacuum. The remaining syrup was dissolved into 25 mL of methylene chloride and washed with 0.1 M HCl until the pH of the aqueous phase was less than 3. The organic phase was dried under anhydrous sodium sulfate, filtered and concentrated to yield a syrup. To this syrup was added 25 mL of aqueous isopropyl alcohol (50 wt%) and the solution was cooled to 0° C. Sodium hydroxide (1 mL of a 1.0 mM solution) was added and stirred at 0° C. for 4 hr. The solution was neutralized with acetic acid, concentrated and filtered through a short plug of silica gel with ether, concentrated and recrystallized from benzene/chloroform to yield 27 mg (0.11 mmol) of N-acetyl serotonin.

Provenance & Evidence