Reaktion #74803

Reaktionsgleichung

1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride

potassium carbonate

benzyl bromide

potassium carbonate

benzyl bromide

→

1-[2-(N-isopropyl-N-benzylamino)-propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is refluxed for 3 hours
2. 2
   TemperaturRefluxing
3. 3
   workup.ADDITIONa second addition of the same reagents
4. 4
   Temperaturrefluxing for an additional day
5. 5
   SonstigeThe mixture is evaporated
6. 6
   workup.ADDITIONthe residue diluted with water
7. 7
   Extraktionextracted with chloroform
8. 8
   Sonstigethe extract dried
9. 9
   Sonstigeevaporated
10. 10
    SonstigeThe crude product is crystallized from petroleum ether
11. 11
    Sonstigerecrystallized from ethanol

Vorschrift

To the solution of 5.0 g of the slow moving 1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride in 66 ml of anhydrous ethanol are added 3.64 g of anhydrous potassium carbonate and 3.14 ml of benzyl bromide. The mixture is refluxed for 3 hours while stirring and half of the original quantities of potassium carbonate and benzyl bromide are added. Refluxing is continued overnight and a second addition of the same reagents and refluxing for an additional day leads to complete benzylation. The mixture is evaporated, the residue diluted with water, extracted with chloroform and the extract dried and evaporated. The crude product is crystallized from petroleum ether and recrystallized from ethanol to give the 1-[2-(N-isopropyl-N-benzylamino)-propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one, melting at 205°-207°.

Quelle