تفاعل #4103

معادلة التفاعل

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

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product

المردود 57.0%

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

المردود 57.0%

المذيبات

phosphorus oxychloride

ظروف التفاعل

المعالجة

1. 1
   أخرىwas obtained
2. 2
   درجة الحرارةheated
3. 3
   درجة الحرارةunder reflux for 40 minutes
4. 4
   درجة الحرارةThe reaction mixture was cooled
5. 5
   أخرىExcess phosphorus oxychloride was removed by evaporation at 50°-55° C
6. 6
   أخرىThe residue was dried for 30 minutes under vacuum
7. 7
   درجة الحرارةIce-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
    أخرىThe organic phase was separated
12. 12
    غسيلwashed with brine (2 times, 200 ml)
13. 13
    تجفيفdried over anhydrous magnesium sulfate
14. 14
    تركيزconcentrated
15. 15
    أخرىCrystallization from ether (100 ml)

الإجراء التجريبي

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.

المصدر