Reaktion #4127

Reaktionsgleichung

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

→

product

Ausbeute 53.9%

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

Ausbeute 53.9%

Lösungsmittel

phosphorus oxychloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 25 minutes under nitrogen
2. 2
   TemperaturThe solution was cooled
3. 3
   Sonstigeexcess phosphorus oxychloride was removed at 55°-60° C. under vacuum
4. 4
   TemperaturIce-chilled 2N-sodium hydroxide solution (100 ml) and dichloromethane (250 ml)
5. 5
   workup.ADDITIONwere added to the residue
6. 6
   SonstigeThe organic phase was separated
7. 7
   Waschenwashed with brine (2 times, 100 ml)
8. 8
   Trocknendried over anhydrous magnesium sulfate
9. 9
   Einengenconcentrated
10. 10
    SonstigePurification
11. 11
    Wascheneluted with dichloromethane (2 l)
12. 12
    workup.ADDITIONThe fractions containing pure material
13. 13
    Einengenconcentrated
14. 14
    SonstigeRecrystallization from isopropanol (30 ml)

Vorschrift

A solution of N-[2-(5-bromo-1-indolinyl)-5-methylphenyl]-4-methyl-1-piperazinecarboxamide (3.3 g, 7.68 mmoles) and phosphorus oxychloride (30 ml) was heated at reflux for 25 minutes under nitrogen. The solution was cooled and excess phosphorus oxychloride was removed at 55°-60° C. under vacuum. Ice-chilled 2N-sodium hydroxide solution (100 ml) and dichloromethane (250 ml) were added to the residue. The organic phase was separated and washed with brine (2 times, 100 ml), dried over anhydrous magnesium sulfate, and concentrated. Purification was accomplished by flash chromatography over aluminum oxide (Grade III, 100 g), eluted with dichloromethane (2 l). The fractions containing pure material were pooled and concentrated. Recrystallization from isopropanol (30 ml) yielded 1.7 g (53.9%) of product, mp 187°-189° C.

Quelle