Pyridine → N-Acetylserotonin

Temperatur

0 °C

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.

1. customN-acetyl serotonin was synthesized
2. customwas terminated
3. customby removing the volatile reagents under high vacuum
4. dissolutionThe remaining syrup was dissolved into 25 mL of methylene chloride
5. washwashed with 0.1 M HCl until the pH of the aqueous phase
6. customThe organic phase was dried under anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customto yield a syrup
10. temperaturethe solution was cooled to 0° C
11. stirringstirred at 0° C. for 4 hr
12. concentrationconcentrated
13. filtrationfiltered through a short plug of silica gel with ether
14. concentrationconcentrated
15. customrecrystallized from benzene/chloroform

ORD-Eintrag

ord-7f8eaa8a4b1b404fbb966f08a57d09ec

Quelldatensatz

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07045543B2