Reaktion #4110

Reaktionsgleichung

4-methyl-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one

N-methylpiperazine

→

product

4-Methyl-7-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepine

Lösungsmittel

Toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturunder reflux for two hours
3. 3
   Sonstigethe insoluble material was removed by filtration
4. 4
   SonstigeThe organic phase was separated
5. 5
   ExtraktionThe aqueous phase was extracted with toluene (200 ml)
6. 6
   WaschenThe combined toluene solutions were washed with water (300 ml), brine (2 times, 300 ml)
7. 7
   Trocknendried over anhydrous sodium sulfate
8. 8
   SonstigeThe solvent was evaporated
9. 9
   SonstigeThe residue was triturated with ethanol
10. 10
    SonstigeRecrystallization of the solid from chloroform

Vorschrift

A solution of 4-methyl-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one (3.6 g, 14.3 mmoles), N-methylpiperazine (16 ml) and toluene (350 ml) was heated to 110° C. Titanium tetrachloride (4.3 ml) was added in three portions in two minute intervals. The mixture was heated under reflux for two hours and cooled to room temperature. Toluene (500 ml) and ice-water (500 m) were added. The mixture was stirred for 30 minutes and the insoluble material was removed by filtration. The organic phase was separated. The aqueous phase was extracted with toluene (200 ml). The combined toluene solutions were washed with water (300 ml), brine (2 times, 300 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated. The residue was triturated with ethanol:hexane to a solid. Recrystallization of the solid from chloroform:hexane yielded 2.4 g of product. The mother liquor was concentrated and the residue was purified on a silica gel column (60 g, 230-400 mesh) to give a second crop of 1.3 g of product (77% overall yield). Recrystallization from 2-propanol gave the analytical sample, mp 173°-174° C.

Quelle