Reaktion #4164

Reaktionsgleichung

N-benzylpiperazine

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

sodium hydroxide

→

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

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated under nitrogen until a solution
2. 2
   Sonstigeresulted
3. 3
   TemperaturThe mixture was heated
4. 4
   Temperaturunder reflux for 3 hours
5. 5
   Sonstigethe layers were separated
6. 6
   ExtraktionThe aqueous phase was extracted further with 300 ml of toluene
7. 7
   Waschenwashed once with 2N sodium hydroxide solution, twice with water
8. 8
   Trocknendried over anhydrous sodium sulfate
9. 9
   Einengenconcentrated in vacuo
10. 10
    Sonstigecrystallized
11. 11
    SonstigeRecrystallization from a solution of dichloromethane (10 ml) to which methanol (50 ml)
12. 12
    workup.ADDITIONwas added
13. 13
    Sonstigeafforded the analytical sample, mp 129°-131° C.

Vorschrift

A stirred mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-one and 1200 ml of toluene was heated under nitrogen until a solution resulted. Then there was added 44.1 g (0.250 mole) of N-benzylpiperazine, followed by 14.2 g (0.0750 mole) of titanium tetrachloride. The mixture was heated under reflux for 3 hours, cooled to room temperature and treated with 500 ml of 2N sodium hydroxide. After stirring vigorously for 15 minutes, the layers were separated. The aqueous phase was extracted further with 300 ml of toluene. The toluene layers were combined, washed once with 2N sodium hydroxide solution, twice with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was taken up in 50 ml of hot methanol, from which 7.00 g (59%) of product crystallized. Recrystallization from a solution of dichloromethane (10 ml) to which methanol (50 ml) was added afforded the analytical sample, mp 129°-131° C.

Quelle