Propargyl bromide → HCID 23468929, compound

Participants

Reaction Steps

2.8 g (0.013 mol) of 4-(2-methyl-5-benzofuranyl)-piperidine (c.f. Example 12) and 2.4 g (0.02 mol) of 2-propynyl bromide are dissolved in a suspension of 10 g of potassium carbonate in 120 ml of methanol and the solution is stirred at room temperature. After 24 hours, a further 0.24 g of 2-propynyl bromide is added and the reaction mixture is stirred at room temperature for a further 24 hours. Thereafter, it is filtered, the residue on the filter is washed with ethyl acetate and the combined filtrates are evaporated to dryness under a waterpump vacuum. The residue is dissolved again in ethyl acetate and the solution is washed three times with water, dried over sodium sulfate and evaporated to dryness under a waterpump vacuum. The resulting residue is chromatographed on 200 g of aluminium oxide (eluting agent: methylene chloride), whereupon, after evaporating off the solvent, crystalline 1-(2-propynyl)-4-(2-methyl-5-benzofuranyl)-piperidine is obtained. The hydrochloride, prepared from the base in a conventional manner, melts at 185°-187°.

Provenance & Evidence