1,1'-Carbonyldiimidazole → 2-Chloro-3-fluoro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

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Reaction Steps

A solution of 2-chloro-3-fluorobenzoic acid (0.098 g) and carbonyldiimidazole (0.091 g), in N,N-dimethylformamide (3.0 ml) was stirred for 2.5 hours at room temperature. 1-Adamantanemethylamine (0.1 ml) was then added and stirring continued overnight. The reaction mixture was partitioned between ethyl acetate and 2N hydrochloric acid and the organic layer was separated, washed with 10% aqueous sodium hydroxide, water and brine and then dried over sodium sulphate (Na2SO4). The organic layer was subsequently concentrated under reduced pressure to yield the tire compound as a white solid (0.138 g).

Provenance & Evidence