Sodium Bicarbonate → 5-HYDROXYFLECAINIDE

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Reaction Steps

The crude product from Example 6 is mixed with 0.3 g of platinum oxide in 250 ml of glacial acetic acid. The mixture is reduced with hydrogen gas in a Parr apparatus. The catalyst is removed by filtration and the filtrate is evaporated to provide a solid residue. This product, 5-hydroxy-N-(2-piperidylmethyl)-2-(2,2,2-trifluoroethoxy)benzamide acetate, is dissolved in water and the aqueous solution is basified with sodium bicarbonate solution. The water solution is then extracted with a large volume of dichloromethane and the dichloromethane extracts are dried over magnesium sulfate. The magnesium sulfate is removed by filtration and the solvent is evaporated to provide a solid product. The product is recrystallized from toluene, treated with charcoal, filtered and rinsed with a toluene-hexane mixture. Another recrystallization from a 1:1 mixture of toluene and hexane provides tan needles of 5-hydroxy-2-(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide, m.p. 134°-137° C.

Provenance & Evidence