Benzyl Bromide → HCID 23468804, compound

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Reaction Steps

The starting material is prepared as follows: (a) 3.08 g (0.01 mol) of 4-(2,3-dimethyl-7-bromo-5-benzofuranyl)-piperidine (c.f. Example 21) are dissolved in 100 ml of tetrahydrofuran, and 1.4 ml of triethylamine and then 1.30 ml (0.0105 mol) of benzyl bromide are added to the solution. A white precipitate thereby forms. The reaction mixture is stirred at room temperature for 31/2 hours. The solvent and excess triethylamine are then removed under a waterpump vacuum and the residue is added to water. The mixture is extracted 3 times with ether and the combined ether solutions are washed once with 2 N sodium hydroxide solution and then twice with water and once with saturated sodium chloride solution. The combined ether solutions are then dried over sodium sulfate and evaporated completely under a waterpump vacuum. 1-Benzyl-4-(2,3-dimethyl-7-bromo-5-benzofuranyl)-piperidine which melts at 86°-91°, is thereby obtained. In the thin layer chromatogram on silica gel using chloroform/5% methanol as the running agent, this product has an Rf value of 0.4. A sample recrystallised from ether/hexane has a melting point of 88°-91°. The product is of sufficient purity for further use.

Provenance & Evidence