반응 #4103

반응 방정식

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

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product

수율 57.0%

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

수율 57.0%

용매

phosphorus oxychloride

반응 조건

후처리

1. 1
   기타was obtained
2. 2
   온도heated
3. 3
   온도under reflux for 40 minutes
4. 4
   온도The reaction mixture was cooled
5. 5
   기타Excess phosphorus oxychloride was removed by evaporation at 50°-55° C
6. 6
   기타The residue was dried for 30 minutes under vacuum
7. 7
   온도Ice-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
    기타The organic phase was separated
12. 12
    세척washed with brine (2 times, 200 ml)
13. 13
    건조dried over anhydrous magnesium sulfate
14. 14
    농축concentrated
15. 15
    기타Crystallization from ether (100 ml)

실험 절차

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.

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