Synthesis method of homopiperony lamine

Abstract

The invention belongs to the field of organic chemical synthesis, and particularly relates to a synthesis method of homopiperony lamine. The synthesis method comprises the following steps: preparing heliotropin by using catechol as a raw material; preparing beta-nitro-3, 4-dioxomethine styrene from heliotropin; and preparing the homopiperony lamine by using the beta-nitro-3, 4-dioxomethylenestyrene. The method for preparing heliotropin by using catechol as the raw material comprises the following two ways: (1) catechol -> 3,4-dihydroxy mandelic acid -> 3, 4-dihydroxy benzaldehyde -> heliotropin; and (2) catechol -> benzodioxole -> heliotropin. The used raw materials are safe, easy to obtain and low in cost; reaction conditions are mild, operation is simple and convenient, chemical yield is high, and intermediate reagents are easy to recover; and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a synthesis method of piperonylethylamine. Background technique [0002] Piperethylamine, the chemical name is 3,4-methylenedioxyphenethylamine, is an important intermediate for the synthesis of dopamine and berberine. The route of synthetic piperonyl ethylamine mainly contains following four kinds at present: [0003] Among them, the following two synthesis processes of piperonyl ethylamine were reported in the "National Compendium of Raw Materials Processes" published by the State Administration of Medicine in 1980. The first is to synthesize piperonylethylamine by using o-diphenol as raw material through etherification ring closure, chloromethylation, amination hydrolysis, Duff reaction epoxidation, hydrolysis, decarboxylation, amination, and catalytic hydrogenation. This method has a long reaction time, many steps and complicated operations, and is not ...

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Problems solved by technology

[0007] Third, many documents (J.Med.Chem.2013,56,9673 and Org.Biomol.Chem.,2012,10,835) have reported a kind of piperonal as raw material, which reacts with nitromethane to generate the corresponding nitromethane However, this route uses lithium aluminum hydride or zinc amalgam as a reducing agent. Lithium aluminum hydride is expensive, and zinc amalgam contains metallic mercury, which is highly toxic and pollutes the environment heavily. , so it is not suitable for large-scale industrial production;

[0009] The fourth type, Chinese patent CN 108164498 A reports a kind of piperonyl ethylamine is obtained through steps such as condensation with cyanoacetic acid, decarboxylation, hydrolysis, Hoffman downgrading reaction, catalytic hydrogenation, etc., using piperonine as raw material, wherein using liquid bromine , metal catalytic hydrogenation and other steps, the cost is high, the labor protection requirements are high, and the production process will generate a large amount of acidic wastewater, which increases the treatment cost of the three wastes, so it is not suitable for industrial production

[0011] In the above-mentioned synthetic methods, on the one hand, there are too many synthetic steps and the operation is cumbersome; on the other hand, most of the reagents used in the synthetic process have disadvantages such as high toxicity, high price, large pollution, and difficult recovery and application.

Therefore limit the industrialized large-scale production of piperonyl ethylamine

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