asynthesisoftropinone托品酮合成-文庫吧資料
2024-08-29 16:29本頁面
【正文】 acetone and methylamine in aqueous solution. An improvement followed on the replacement of the acetone by a salt of acetonedicarboxylic acid. The initial product is a salt of tropinonedicarboxylic acid, and this loses two molecules of carbon dioxide with the formation of tropinone when the solution is acidified and heated. Tropinone was also obtained by the hydrolysis of the product of condensation of succindialdehyde with ethyl acetonedicarboxylate and methylamine in alcoholic solution. When more material is available it is hoped to institute a series of experiments with the object of defining the optimum conditions of the synthesis, and it will then be possible to state with more exactness the maximum yield obtainable. However, in spite of the small experience so far gained, an experiment is described in which the yield of dipiperonylideropinone from succindialdehyde was 42 per cent. of that theoretically possible. The method of synthesis of bicyclic bases which has been developed is probably of general application, and an attempt will be made to synthesise ?pelletierine by the condensation of glutardialdehyde with methylamine and a derivative of acetone. Experimental Dipiperonylideropinone(Formula II) Potassium hydroxide(5g) dissolved in water (20ml) was added to tropinone (2g) and piperonal (6g) dissolved in alcohol (100ml) , and the solution was then boiled under reflux during fifteen minutes. The derivative crystallized during the course of the reaction, and, after the addition of water, was collected, washed with water and alcohol, and crystallized from ethyl acetate. The yield was quantitative: Dipiperonylideropinone separates from ethyl acetate in bright yellow needles melting at 214, and is sparingly soluble in most anic solvents. If it is rubbed on the side of a testtube and sulphuric acid added, the substance acquires a coppery lustre and then passes into an intense royalblue solution. This bees green and finally yellow on dilution with water. The salts of the substance are in general sparingly soluble, but the acetate dissolves readily in water to a bright orangeyellow solution. Yellow, crystalline precipitates of corresponding salts are obtained on the addition to such a solution of hydrochloric, hydrobromic, nitric, sulphuric, oxalic, or picric acid. The hydrochloride crystallises from hot water, in which it is sparingly soluble, in yellow, microscopic needles. The substance is deposed by hydroxylamine in boiling alcoholic solution with the formation of piperonaloxime, and presumably of the oxime of tropinone. The formation o
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