反応 #216960

反応方程式

propyl iodide

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

Acetonitrile

K2CO3

→

desired product

収率 80.0%

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

収率 80.0%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他equipped with a mechanical stirrer, condenser
2. 2
   その他topped with a nitrogen inlet
3. 3
   洗浄washed successively with H2O, NaHCO3 solution, H2O, brine
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過After filtration
6. 6
   その他the volatiles were removed in vacuo
7. 7
   その他to provide 11.5 g (94%) crude product
8. 8
   その他This material was then recrystallized from 95% ethanol

実験手順

(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%).

出典