Hydrochloric Acid → 4-amino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide

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Reaction Steps

4-tert-Butoxycarbonylamino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide (80.0 mg) was mixed with a 4 mol/L dioxane solution of hydrogen chloride (1.2 mL) and the mixture was stirred at room temperature for 40 minutes. The crystallized product was collected by filtration and was suspended in water (0.8 mL). While the suspension was chilled in an ice bath, a 1 mol/L aqueous solution of sodium hydroxide (0.3 mL) was added and the mixture was extracted with dichloromethane (4×3 mL). The dichloromethane extracts were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. This gave 4-amino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide (39.8 mg) as a white solid.

Provenance & Evidence