4-Bromoaniline → N-(4-Bromophenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide Hydrochloride

Participants

Reaction Steps

1.00 g (4.76 mmol) of 3-quinuclidinecarbonyl chloride hydrochloride is added at 0° C. to a solution of 900 mg (5.24 mmol) of 4-bromoaniline and 1.85 g (14.28 mmol) of N,N-diisopropylethylamine in about 10 ml of dry DMF. The mixture is stirred at room temperature overnight. Purification by preparative HPLC is followed by chromatography again on silica gel (mobile phase: dichloromethane/methanol/triethylamine 80:20:2). The product is dissolved in methanol and mixed with 1N HCl in methanol. Finally, the solvent is removed. 0.63 g (31% of theory) of the title compound is obtained. The raw material is employed directly in the next synthesis.

Provenance & Evidence