反応 #4127

反応方程式

N-[2-(5-bromo-1-indolinyl)-5-methylphenyl]-4-methyl-1-piperazinecarboxamide

→

product

収率 53.9%

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

収率 53.9%

溶媒

phosphorus oxychloride

反応条件

後処理

1. 1
   温度at reflux for 25 minutes under nitrogen
2. 2
   温度The solution was cooled
3. 3
   その他excess phosphorus oxychloride was removed at 55°-60° C. under vacuum
4. 4
   温度Ice-chilled 2N-sodium hydroxide solution (100 ml) and dichloromethane (250 ml)
5. 5
   workup.ADDITIONwere added to the residue
6. 6
   その他The organic phase was separated
7. 7
   洗浄washed with brine (2 times, 100 ml)
8. 8
   乾燥dried over anhydrous magnesium sulfate
9. 9
   濃縮concentrated
10. 10
    その他Purification
11. 11
    洗浄eluted with dichloromethane (2 l)
12. 12
    workup.ADDITIONThe fractions containing pure material
13. 13
    濃縮concentrated
14. 14
    その他Recrystallization from isopropanol (30 ml)

実験手順

A solution of N-[2-(5-bromo-1-indolinyl)-5-methylphenyl]-4-methyl-1-piperazinecarboxamide (3.3 g, 7.68 mmoles) and phosphorus oxychloride (30 ml) was heated at reflux for 25 minutes under nitrogen. The solution was cooled and excess phosphorus oxychloride was removed at 55°-60° C. under vacuum. Ice-chilled 2N-sodium hydroxide solution (100 ml) and dichloromethane (250 ml) were added to the residue. The organic phase was separated and washed with brine (2 times, 100 ml), dried over anhydrous magnesium sulfate, and concentrated. Purification was accomplished by flash chromatography over aluminum oxide (Grade III, 100 g), eluted with dichloromethane (2 l). The fractions containing pure material were pooled and concentrated. Recrystallization from isopropanol (30 ml) yielded 1.7 g (53.9%) of product, mp 187°-189° C.

出典