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High-yield oxapium iodide preparation method

A technology of oxalidium and high yield, which is applied in the field of preparation of high-yield oxalidium, can solve the problems of being unable to adapt to industrialized production, unsuitable for industrialized production, low yield of oxalidium, and the like, and achieves a technological The reaction time is short, the product purification method is simple, and the effect of increasing the comprehensive yield and purity

Inactive Publication Date: 2017-04-12
HEFEI PINGGUANG PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In foreign countries, only Japanese patents JP: 56-25175, JP: 56-30971 and JP: 56-71089 have been described, and their common characteristics are all based on 2-cyclohexyl-2-phenyl-4-p-toluenesulfonate Acyloxy-1,3-dioxolane is used as the starting material, which is not easy to obtain. At the same time, column chromatography technology is required to separate the intermediate during the purification process, which cannot meet the requirements of industrial production
[0004] Disclosed in the Chinese patent CN101121708B is a preparation method of high-yield oxalate ammonium iodide, using cyclohexyl phenyl ketone and 3-chloro-1,2 propanediol as reaction raw materials, raw materials are cheap and easy to get, but the yield of intermediates Lower, finally cause the yield of oxalium iodide ammonium on the low side, and the reaction time is longer, is not suitable for suitability for suitability for suitability for industrialized production

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preparation example Construction

[0022] Reference figure 1 , The method for preparing oxalidomium with high yield provided by the present invention includes the following steps:

[0023] S1. Preparation of 2-phenyl-2-cyclohexyl-4-bromomethyl-1,3-dioxane: add boron trifluoride ether complex dropwise to dry cyclohexyl phenyl ketone, adjust Temperature, drip dry 1-bromo-2,3-epoxypropane, continuously stir during the dripping process, adjust the temperature, continue stirring, under reduced pressure distillation of boron trifluoride ether complex and cyclohexyl phenyl ketone to obtain Material A; Material A is purified and dried to obtain 2-phenyl-2-cyclohexyl-4-bromomethyl-1,3-dioxolene;

[0024] S2. Preparation of 2-phenyl-2-cyclohexyl-4-piperidinemethyl-1,3-dioxolone: ​​the piperidine, the second organic solvent, the catalyst and the 2-phenyl-2- Mix and dissolve cyclohexyl-4-bromomethyl-1,3-dioxane; adjust the temperature to 25-35℃, keep stirring for 4-6h, and concentrate under reduced pressure to obtain material...

Embodiment 1

[0028] A method for preparing high-yield oxalinium ammonium includes the following steps:

[0029] S1. Preparation of 2-phenyl-2-cyclohexyl-4-bromomethyl-1,3-dioxane: Add 0.84 parts of boron trifluoride ether complex dropwise to 75 parts of dry cyclohexyl by weight In the phenyl ketone, adjust the temperature to 0°C, add dropwise 41 parts of 1-bromo-2,3-epoxypropane dry, stir continuously during the dropping process, adjust the temperature to 5°C, continue to stir for 7h, at 80 Distill boron trifluoride ether complex and cyclohexyl phenyl ketone under reduced pressure at a temperature of ℃ to obtain material A; add material A to ethanol to recrystallize and dry to obtain 2-phenyl-2-cyclohexyl-4-bromide Methyldioxane;

[0030] S2. Preparation of 2-phenyl-2-cyclohexyl-4-piperidinylmethyl-1,3-dioxolone: ​​According to parts by weight, 51 parts of piperidine, 450 parts of ethanol, 2.7 parts of aluminum trichloride and S1 The obtained 32 parts of 2-phenyl-2-cyclohexyl-4-bromomethyl-1,...

Embodiment 2

[0033] A method for preparing high-yield oxalinium ammonium includes the following steps:

[0034] S1. Preparation of 2-phenyl-2-cyclohexyl-4-bromomethyl-1,3-dioxane: 1.14 parts of boron trifluoride ether complex are added dropwise to 56 parts of cyclohexyl by weight In the phenyl ketone, adjust the temperature to 5°C, add dropwise 27 parts of dry 1-bromo-2,3-epoxypropane, keep stirring during the dropping process, adjust the temperature to 15°C, continue to stir for 5h, at 90 Distill boron trifluoride ether complex and cyclohexyl phenyl ketone under reduced pressure at a temperature of ℃ to obtain material A; add material A to acetonitrile to recrystallize and dry to obtain 2-phenyl-2-cyclohexyl-4-bromide Methyldioxane;

[0035] S2. Preparation of 2-phenyl-2-cyclohexyl-4-piperidinylmethyl-1,3-dioxolone: ​​34 parts of piperidine, 750 parts of ethanol, 1.7 parts of ferric chloride and S1 The obtained 65 parts of 2-phenyl-2-cyclohexyl-4-bromomethyl-1,3-dioxane were mixed and dissol...

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Abstract

The invention discloses a high-yield oxapium iodide preparation method, which comprises: S1, preparing 2-phenyl-2-cyclohexyl-4-bromomethyl-1,3-dioxole: adding a boron trifluoride diethyl ether complex to dried cyclohexyl phenyl ketone in a dropwise manner, adjusting the temperature, adding dried 1-bromo-2,3-epoxypropane in a dropwise manner, continuously stirring during the adding, adjusting the temperature, continuously stirring, carrying out pressure reducing distillation on the boron trifluoride diethyl ether complex and the cyclohexyl phenyl ketone to obtain a material A, purifying the material A, and drying to obtain the 2-phenyl-2-cyclohexyl-4-bromomethyl-1,3-dioxole; S2, preparing 2-phenyl-2-cyclohexyl-4-piperidinomethyl-1,3-dioxole; and S3, preparing oxapium iodide. According to the present invention, the preparation method has characteristics of mild reaction condition, cheap and easily-available raw materials, low cost, high product purity and good comprehensive yield, and is suitable for industrial production.

Description

Technical field [0001] The invention relates to the technical field of oxalinium synthesis, in particular to a method for preparing oxalinium with high yield. Background technique [0002] Oxalidomide is an antispasmodic drug developed by Taisho Toyama Pharmaceutical Company in Japan. It was listed in Japan in June 1984 under the trade name This variety is included in the Japanese Pharmacopoeia XIV edition. This product is clinically mainly used to treat pain caused by female genital spasm, gastrointestinal spasm, urethral spasm, biliary spasm, and movement disorders. [0003] At present, there is no relevant literature report about the preparation method of oxalinium and its analogues. In foreign countries, only the Japanese Open Patent JP: 56-25175, JP: 56-30971 and JP: 56-71089 have related explanations, and their common characteristics are all based on 2-cyclohexyl-2-phenyl-4-p-toluenesulfonate Acyloxy-1,3-dioxolane is the starting material, which is not easy to obtain. At t...

Claims

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Application Information

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IPC IPC(8): C07D317/28
CPCC07D317/28
Inventor 王康林黄志生张成栋柏春雷
Owner HEFEI PINGGUANG PHARMA
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