반응 #4196

반응 방정식

4-methyl-N-[2-(6-bromo-1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazine-carboxamide

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product

수율 79.0%

5-Bromo-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]benzodiazepine

수율 79.0%

용매

phosphorus oxychloride

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux under nitrogen for 5 hours
3. 3
   기타excess phosphorous oxychloride was removed at aspirator pressure
4. 4
   온도with heating
5. 5
   온도The residue was chilled in an ice-bath (with exclusion of moisture)
6. 6
   workup.ADDITIONtreated with ice-cold 2N sodium hydroxide solution (250 ml) and dichloromethane (500 ml)
7. 7
   기타the organic phase was separated
8. 8
   세척washed with 2N sodium hydroxide solution, twice with water
9. 9
   건조dried over anhydrous sodium sulfate
10. 10
    농축concentrated in vacuo

실험 절차

A stirred mixture of 4-methyl-N-[2-(6-bromo-1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazine-carboxamide (14.2 g, 0.0330 mole) in phosphorus oxychloride (250 ml) was heated under reflux under nitrogen for 5 hours. The reaction mixture was cooled to room temperature and excess phosphorous oxychloride was removed at aspirator pressure with heating. The residue was chilled in an ice-bath (with exclusion of moisture), and treated with ice-cold 2N sodium hydroxide solution (250 ml) and dichloromethane (500 ml). The mixture was stirred, the organic phase was separated, washed with 2N sodium hydroxide solution, twice with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was digested in boiling methanol (40 ml) to afford 10.7 g (79%) of product. Recrystallization from ethanol provided the analytical sample, mp 181°-183° C.

출처