Reaktion #330820

Reaktionsgleichung

compound V

2-(7-methoxy-1-naphthyl)ethylamine Hydrochloride

potassium carbonate

acetyl chloride

→

agomelatine

Ausbeute 78.5%

Lösungsmittel

water

dichloromethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe aqueous layer was removed
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   workup.WAITto proceed at room temperature for 1 hour
4. 4
   Extraktionthe reaction solution was extracted with dichloromethane (50 ml*3)
5. 5
   Trocknendried with anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigeto remove the drying agent
8. 8
   EinengenThe filtrate was concentrated under reduced pressure
9. 9
   Sonstigeto give a solid
10. 10
    SonstigeThe solid was recrystallized in a 2:1 toluene/n-hexane mixture

Vorschrift

The compound V (6.0 g, 0.03 mol) produced as described above and potassium carbonate (5 g) were added to 20 ml of water and 40 ml of dichloromethane, and stirred for 30 minutes. The aqueous layer was removed. The organic layer was cooled to the temperature of 0° C., and acetyl chloride (7.8 g, 0.1 mol) was added dropwise. A reaction was allowed to proceed at room temperature for 1 hour. 100 ml water was then added, and the reaction solution was extracted with dichloromethane (50 ml*3). The organic phases were combined, dried with anhydrous magnesium sulfate, and filtered to remove the drying agent. The filtrate was concentrated under reduced pressure, to give a solid. The solid was recrystallized in a 2:1 toluene/n-hexane mixture, to produce 4.8 g of agomelatine. The yield was 78.5%. The melting point was 107-108° C. (in Literature [2], 109° C.).

Quelle