2-Chloroacetophenone → (3R)-3-(2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride

Participants

Reaction Steps

(R)-Quinuclidin-3-yl 2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetate (169 mg, 0.47 mmol) was dissolved in a mixture of ethyl acetate (3 ml) and acetonitrile (1.5 ml). 2-Chloro-1-phenylethanone (80 mg, 0.52 mmol) was added and the reaction was stirred at room temperature for 5 hours. The solvent was evaporated and the residue was triturated with EtOAc (10 ml). The product was purified by flash chromatography (DCM/MeOH=9/1 to 85/15) to obtain (3R)-3-(2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (99 mg, 0.193 mmol, 40.9% yield) as a pale yellow spongy solid.

Provenance & Evidence