反応 #4196

反応方程式

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

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product

収率 79.0%

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

収率 79.0%

溶媒

phosphorus oxychloride

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度under reflux under nitrogen for 5 hours
3. 3
   その他excess phosphorous oxychloride was removed at aspirator pressure
4. 4
   温度with heating
5. 5
   温度The 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
   その他the organic phase was separated
8. 8
   洗浄washed with 2N sodium hydroxide solution, twice with water
9. 9
   乾燥dried over anhydrous sodium sulfate
10. 10
    濃縮concentrated in vacuo

実験手順

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.

出典