반응 #4094

반응 방정식

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

→

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

수율 37.0%

용매

phosphorus oxychloride

반응 조건

후처리

1. 1
   기타The excess phosphorus oxychloride was removed at aspirator pressure with gentle warming
2. 2
   온도The residue was chilled in an ice-bath (with exclusion of moisture)
3. 3
   workup.ADDITIONtreated first with 250 ml of ice-cold 2N-NaOH
4. 4
   기타The organic phase was separated
5. 5
   세척washed four times with water
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated in vacuo to 5.7 g (95%) of a semi-crystalline material
8. 8
   기타Recrystallization from acetone

실험 절차

A stirred solution of 6.30 g (0.017 mole) of N-[5-chloro-2-(2,3-dihydro-1H-indol-1-yl)-phenyl]-4-methyl-1piperazinecarboxamide of Example 4b in 100 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 250 ml of dichloromethane. The mixture was stirred vigorously until all the material passed into solution. The organic phase was separated, washed four times with water, dried over Na2SO4 and concentrated in vacuo to 5.7 g (95%) of a semi-crystalline material. Recrystallization from acetone afforded 2.20 g (37% overall yield) of 9-chloro-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine, m.p. 154°-156° C.

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