Hydrochloric Acid → HCID 18654742, compound

Temperature

-78 °C

To a stirred solution of 12.8 g (29 mmol) of (+)(2aR,4S)-1-benzoyl-6-bromo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 200 ml of tetrahydrofuran cooled to -78° C. under a nitrogen atmosphere was added 20 ml (32 mmol) of a 1.6M solution of n-butyllithium in hexane. The reaction mixture was stirred at -78° C. for 30 minutes and then allowed to warm to -20° C. To the reaction mixture was added 50 ml of a 1N hydrochloric acid solution. The mixture was extracted once with diethyl ether. The acidic solution was made alkaline with the addition of cold 5N sodium hydroxide solution. The basic mixture was extracted twice with methylene chloride. The combined organic solution was washed with a saturated sodium chloride solution. The methylene chloride solution was dried over magnesium sulfate and evaporated to give 9.6 g of (-)(2aR,4S)-6-bromo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole.

1. temperatureto warm to -20° C
2. extractionThe mixture was extracted once with diethyl ether
3. additionwith the addition of cold 5N sodium hydroxide solution
4. extractionThe basic mixture was extracted twice with methylene chloride
5. washThe combined organic solution was washed with a saturated sodium chloride solution
6. dry with materialThe methylene chloride solution was dried over magnesium sulfate
7. customevaporated

ORD record

ord-f3ec389a6f504b71b1ed6aef296f55b0

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05656653