Acetonitrile → (+)(2aR,4S)-1-benzoyl-6-bromo-4-(di-n-propylamino)1,2,2a,3,4,5-hexahydrobenz[cd]indole

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Reaction Steps

(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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