تفاعل #4138

معادلة التفاعل

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

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product

المردود 79.0%

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

المردود 79.0%

المذيبات

phosphorus oxychloride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةunder reflux under nitrogen for 5 hours
3. 3
   أخرىexcess phosphorous oxychloride was removed at aspirator pressure
4. 4
   درجة الحرارةwith heating
5. 5
   درجة الحرارةThe 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
   أخرىthe organic phase was separated
8. 8
   غسيلwashed with 2N sodium hydroxide solution, twice with water
9. 9
   تجفيفdried over anhydrous sodium sulfate
10. 10
    تركيزconcentrated in vacuo

الإجراء التجريبي

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.

المصدر