반응 #4096

반응 방정식

N-[5-methyl-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide

→

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

수율 41.0%

용매

phosphorus oxychloride

반응 조건

후처리

1. 1
   온도was refluxed for 6 hours under nitrogen
2. 2
   기타The excess phosphorus oxychloride was removed at aspirator pressure with gentle warming
3. 3
   온도The residue was chilled in an ice-bath (with exclusion of moisture)
4. 4
   workup.ADDITIONtreated first with 250 ml of ice-cold 2N-NaOH
5. 5
   기타The organic phase was separated
6. 6
   세척washed thrice with water
7. 7
   농축concentrated in vacuo to an oil
8. 8
   workup.DISSOLUTIONThis was dissolved in 100 ml of boiling acetone
9. 9
   기타to crystallize at room temperature

실험 절차

A stirred mixture of 35.1 (0.10 mole) of N-[5-methyl-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide of Example 5c in 500 ml of phosphorus oxychloride was refluxed for 6 hours under nitrogen, then cooled to room temperature. The excess phosphorus oxychloride was removed at aspirator pressure with gentle warming. The residue was chilled in an ice-bath (with exclusion of moisture), and then treated first with 250 ml of ice-cold 2N-NaOH, then with 500 ml of chloroform. The mixture was stirred vigorously until all the material passed into solution. The organic phase was separated, washed thrice with water, and concentrated in vacuo to an oil. This was dissolved in 100 ml of boiling acetone, then allowed to crystallize at room temperature to afford 13.5 g (41% overall yield) of 9-methyl-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]-benzodiazepine, m.p. 160°-162° C.

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