Reaktion #4113

Reaktionsgleichung

morpholine

9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one

sodium hydroxide

→

9-Bromo-6-(4-morpholinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated under nitrogen
2. 2
   Sonstigeresulted
3. 3
   TemperaturThe mixture was heated
4. 4
   Temperaturunder reflux for three hours
5. 5
   workup.STIRRINGAfter stirring vigorously for 15 minutes
6. 6
   Sonstigethe layers were separated
7. 7
   ExtraktionThe aqueous phase was extracted with 250 ml of toluene
8. 8
   Waschenwashed once with 2N sodium hydroxide solution, twice with water
9. 9
   Trocknendried over anhydrous sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated in vacuo to 8.6 g (90%) of product
12. 12
    SonstigeRecrystallization from a hot solution of dichloromethane (80 ml) to which methanol (80 ml)
13. 13
    workup.ADDITIONwas added
14. 14
    Sonstigeprovided the analytical sample, mp 216°-218° C.

Vorschrift

A mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1200 ml of toluene was heated under nitrogen, with stirring, until a solution resulted. Then there was added 21.8 g (0.250 mole) of morpholine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mixture was heated under reflux for three hours, cooled to room temperature and treated with 500 ml of 2N sodium hydroxide solution. After stirring vigorously for 15 minutes, the layers were separated. The aqueous phase was extracted with 250 ml of toluene. The toluene layers were combined, washed once with 2N sodium hydroxide solution, twice with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to 8.6 g (90%) of product. Recrystallization from a hot solution of dichloromethane (80 ml) to which methanol (80 ml) was added provided the analytical sample, mp 216°-218° C.

Quelle