反応 #63390

反応方程式

N-[2-(5-chloro-1-indolinyl)phenyl]-4-methyl-1-piperazinecarboxamide

1,2-dichloroethane

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product

収率 29.5%

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

収率 29.5%

溶媒

dichloromethane

反応条件

後処理

1. 1
   温度The solution was cooled
2. 2
   その他The layers were separated
3. 3
   洗浄The organic layer was washed with 2 l of 2N sodium hydroxide
4. 4
   乾燥with brine (500 ml), and dried over anhydrous magnesium sulfate
5. 5
   その他Removal of the solvent at reduced pressure
6. 6
   その他gave an oil
7. 7
   その他The oil was purified by flash chromatography on a silica gel column (1 kg, 230-400 mesh)
8. 8
   洗浄eluted initially with dichloromethane

実験手順

To N-[2-(5-chloro-1-indolinyl)phenyl]-4-methyl-1-piperazinecarboxamide (13.5 g, 36.5 mmoles) was added a solution of polyphosphoric acid ethyl ester and 1,2-dichloroethane (250 ml) The solution was heated at 75° C. for 4 hours with exclusion of moisture. The solution was cooled and poured into a mixture of ice-sodium hydroxide solution (2 l) and dichloromethane (1.2 l). The mixture was stirred for 15 minutes. The layers were separated. The organic layer was washed with 2 l of 2N sodium hydroxide, then with brine (500 ml), and dried over anhydrous magnesium sulfate. Removal of the solvent at reduced pressure gave an oil. The oil was purified by flash chromatography on a silica gel column (1 kg, 230-400 mesh), packed and eluted initially with dichloromethane, then with dichloromethane containing an increasing methanol content in 1% increments to a final content of 5% (total 8 l). Concentration of the 5% methanol/dichloromethane eluent gave 3.8 g (28%) of product. Recrystallization from 2-propanol (50 ml) gave the analytical sample, mp 182°-183° C.

出典