Hydrochloric Acid → HCID 70041994, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyllithium in hexane (2.7 mmol) was added dropwise at -70° C. to a solution of (RS)-N-(1-azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-9H-benzocycloheptene-1-carboxamide (0.37 g, 1.2 mmol), prepared as in Example 5, in dry tetrahydrofuran (10 mL). The reaction mixture was stirred at -10° C. for one hour, cooled to -70° C., and dimethylformamide (1.5 mmol) was added in one portion. The reaction mixture was allowed to warm to room temperature over 1.5 hours, then cooled to 0° C. and acidified with 10% aqueous hydrochloric acid. The layers were separated, and the aqueous layer was washed with ethyl acetate, then made basic with aqueous ammonium hydroxide. The ethyl acetate was dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated to give 0.15 g (40% yield) of (RS)-2-(1-azabicyclo-[2.2.2]oct-3-yl)-1,2,4,5,6,7-hexahydrocyclohept[de]isoquinolin-1-one as a foam. Crystallization from ethanolic hydrochloric acid gave the hydrochloride salt, m.p. >285° C.

Provenance & Evidence