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A kind of synthetic method of palladium catalyzed 5-trifluoromethylpiperonal

A kind of technology of trifluoromethyl piperonal, palladium catalyst, applied in directions such as organic chemistry

Active Publication Date: 2015-12-16
TIANJIN TASLY PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, in the preparation process of 5-trifluoromethylpiperonal, difficulties have been encountered. Because the trifluoromethylation reaction is affected by factors such as trifluoromethylation reagents, reaction conditions and by-products, trifluoromethyl The synthesis of piperonal derivatives remains an important topic

Method used

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  • A kind of synthetic method of palladium catalyzed 5-trifluoromethylpiperonal
  • A kind of synthetic method of palladium catalyzed 5-trifluoromethylpiperonal
  • A kind of synthetic method of palladium catalyzed 5-trifluoromethylpiperonal

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of 5-iodopiperonal:

[0038] Using N,N-dimethylformamide as solvent, add 1.0 equivalent of 5-iodo-3,4-dihydroxybenzaldehyde, 1.5-3.0 equivalent of CH 2 I 2 and 2.0-4.0 equivalents of K 2 CO 3 , heated to 120 ° C for 6-10 hours; the reaction solution was filtered and the filtrate was evaporated to dryness, separated by column chromatography, and the eluent was a mixture of petroleum ether and ethyl acetate with a volume ratio of 10:1 to obtain a white solid that is 5 - Iodopiperonal.

[0039] The preparation method of 5-iodo-3,4-dihydroxybenzaldehyde: use 1,2-dichloroethane as solvent, add 1.0 equivalent of 5-iodo-vanillin to the reaction vessel, and cool to 0°C in an ice bath , adding 2.5 equivalents of AlCl 3 and 10.0 equivalents of pyridine, heated to reflux for 2-4 hours; 20% hydrochloric acid was added to the reaction solution, the organic phase was separated, the aqueous phase was extracted with ethyl acetate, and the combined organic phases were e...

Embodiment 2

[0040] Embodiment 2: the synthesis of 5-trifluoromethyl piperonal

[0041] Under nitrogen protection, add 30ml of N,N-dimethylformamide, 1.0g of 5-iodopiperonal, and 6.9g of FSO into a 50ml three-necked flask 2 CF 2 COOCH 3 , 3.4 grams of cuprous iodide, 0.12 grams of palladium chloride heated to 100 ℃ for 10 hours; A mixture of ether and ethyl acetate gave 0.7 g (87%) of 5-trifluoromethylpiperonal as a white solid.

Embodiment 3

[0042] Embodiment 3: the synthesis of 5-trifluoromethyl piperonal

[0043] Under nitrogen protection, add 30ml of N,N-dimethylformamide, 1.0g of 5-iodopiperonal, and 3.45g of FSO into a 50ml three-necked flask 2 CF 2 COOCH 3 , 1.7 grams of cuprous iodide and 0.06 grams of palladium chloride were heated to 100 ° C for 10 hours; the reaction solution was filtered through diatomaceous earth, and the filtrate was evaporated to dryness and separated by column chromatography. A mixture of ether and ethyl acetate gave 0.65 g (83%) of 5-trifluoromethylpiperonal as a white solid.

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Abstract

The invention relates to a palladium-catalyzed 5-trifluoromethylpiperonal synthesis method. The method comprises the following steps: heating 1.0 part of 5-iodopiperonal, 5.0-10.0 parts of FSO2CF2COOCH3, 2.5-5.0 parts of a halogenated cuprous salt, and 0.1-0.2 parts of a palladium catalyst in a solvent N,N-dimethylformamide to 100DEG C under the protection of nitrogen, and reacting for 8-16h; and filtering the obtained reaction solution through diatomite, drying the obtained filtrate, separating the dried filtrate through column chromatography through using a petroleum ether-ethyl acetate mixed liquor as an eluate according to a volume ratio of 10:1 to obtain a white solid which is 5-trifluoromethylpiperonal.

Description

technical field [0001] The invention relates to the field of organic synthesis of pharmaceutical intermediates, in particular to a method for synthesizing the pharmaceutical intermediate 5-trifluoromethylpiperonal. Background technique [0002] Piperonal derivatives are important organic intermediates, which are widely used in fine chemical fields such as perfumes, fragrances, pesticides, and medicines. They provide important components for the development of new biologically active compounds. For example: 6-aminopiperonal is an important pharmaceutical intermediate, which is used in antimalarial drugs, anti-senile dementia drugs, antihypertensive and antipsychotic drugs; piperine with sedative, antiepileptic and antidepressant effects It can also be synthesized by piperonal. Therefore, the synthesis of piperonal derivatives has been paid close attention to by people. [0003] The derivatives of piperonal having a leaving functional group at the 5-position have good applic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/54
Inventor 韩民王亚虎靳元鹏马晓慧周水平张兰兰王国成朱永宏
Owner TIANJIN TASLY PHARMA CO LTD