Reaktion #4161

Reaktionsgleichung

N-[2-(5-bromo-1-indolinyl)phenyl]-4-methyl-1-piperazinecarboxamide

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product

Ausbeute 57.0%

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

Ausbeute 57.0%

Lösungsmittel

phosphorus oxychloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas obtained
2. 2
   Temperaturheated
3. 3
   Temperaturunder reflux for 40 minutes
4. 4
   TemperaturThe reaction mixture was cooled
5. 5
   SonstigeExcess phosphorus oxychloride was removed by evaporation at 50°-55° C
6. 6
   SonstigeThe residue was dried for 30 minutes under vacuum
7. 7
   TemperaturIce-chilled 2N sodium hydroxide solution (250 ml) and dichloromethane (350 ml)
8. 8
   workup.ADDITIONwere added to the residue at 4° C. (ice-water bath)
9. 9
   workup.STIRRINGThe mixture was stirred until all the solid
10. 10
    workup.DISSOLUTIONhad dissolved
11. 11
    SonstigeThe organic phase was separated
12. 12
    Waschenwashed with brine (2 times, 200 ml)
13. 13
    Trocknendried over anhydrous magnesium sulfate
14. 14
    Einengenconcentrated
15. 15
    SonstigeCrystallization from ether (100 ml)

Vorschrift

A mixture of N-[2-(5-bromo-1-indolinyl)phenyl]-4-methyl-1-piperazinecarboxamide (11.5 g, 27.5 mmoles) and 750 ml of phosphorus oxychloride was stirred until a solution was obtained and then heated under reflux for 40 minutes. The reaction mixture was cooled. Excess phosphorus oxychloride was removed by evaporation at 50°-55° C. The residue was dried for 30 minutes under vacuum. Ice-chilled 2N sodium hydroxide solution (250 ml) and dichloromethane (350 ml) were added to the residue at 4° C. (ice-water bath). The mixture was stirred until all the solid had dissolved. The organic phase was separated and washed with brine (2 times, 200 ml), dried over anhydrous magnesium sulfate and concentrated. Crystallization from ether (100 ml) gave 5.7 g (57%) of product. Recrystallization from isopropanol yielded the analytical sample, mp 203°-204° C.

Quelle