반응 #216960

반응 방정식

propyl iodide

(2aR, 4S)-1-Benzoyl-4-amino-6-bromo-1,2,2a,3,4,5-hexahydrobenz[cd]indole

Acetonitrile

K2CO3

→

desired product

수율 80.0%

(2aR, 4S)-1-Benzoyl-4-(di-n-propyl)amino-6-bromo-1,2,2a,3,4,5-hexahydrobenz[cd]indole

수율 80.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타equipped with a mechanical stirrer, condenser
2. 2
   기타topped with a nitrogen inlet
3. 3
   세척washed successively with H2O, NaHCO3 solution, H2O, brine
4. 4
   건조dried over Na2SO4
5. 5
   여과After filtration
6. 6
   기타the volatiles were removed in vacuo
7. 7
   기타to provide 11.5 g (94%) crude product
8. 8
   기타This material was then recrystallized from 95% ethanol

실험 절차

(2aR, 4S)-1-Benzoyl-4-amino-6-bromo-1,2,2a,3,4,5-hexahydrobenz[cd]indole (9.82 g, 0.0275 mol) was placed in 500 ml round bottom flask equipped with a mechanical stirrer, condenser topped with a nitrogen inlet, and a thermocouple. Acetonitrile (175 ml) and K2CO3 (0.275 mol) were added, followed by the addition of propyl iodide (13.2 ml, 0.137 mol) with vigorous stirring. The reaction mixture was stirred at 75°±5° C. under nitrogen overnight. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2 (200 ml) and washed successively with H2O, NaHCO3 solution, H2O, brine and dried over Na2SO4. After filtration, the volatiles were removed in vacuo to provide 11.5 g (94%) crude product. This material was then recrystallized from 95% ethanol to provide the desired product as colorless needles 9.7 g (80.0%).

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