Method for preparing 3-pyridine acetic acid hydrochloride

A technology of pyridine acetic acid hydrochloride and pyridine thioacetyl, which is applied in the synthesis field of pharmaceutical intermediate 3-pyridine acetic acid hydrochloride, can solve the problems of metallic sodium such as danger, difficulty in storage, complicated post-processing, etc., and achieve The effect of shortening the preparation process, easy operation and improving product quality

Inactive Publication Date: 2008-02-06
潍坊祥维斯化学品有限公司
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  • Abstract
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Problems solved by technology

But the first step reaction needs to use sodium hydride and sodium methylate (or sodium ethylate) in this method, yield 81-85%, sodium hydride price is more expensive, and sodium methylate (or sodium ethylate) is difficult for preservation
The last step is hydrolysis with alkali, the post-treatment is more complicated, sodium chloride is difficult to remove, the yield is 74%, mp153-155°C
[0005] I

Method used

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  • Method for preparing 3-pyridine acetic acid hydrochloride
  • Method for preparing 3-pyridine acetic acid hydrochloride

Examples

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Example Embodiment

[0020] Example 1

[0021] a) Preparation steps of 3-pyridinethioacetylmorpholine

[0022] Add 86.8g of 3-vinylpyridine to 79g of morpholine, add 29g of sulfur while stirring, heat and reflux for reaction for 12 hours, pour the reactant into ice water and filter, wash the crystals with ice water, and dry naturally in the air to get light yellow The crystal was 160.2g, and the yield was 87.3%.

[0023] b) Preparation steps of 3-pyridineacetic acid hydrochloride

[0024] Mix 160.2g of 3-pyridinethioacetylmorpholine with 182ml of hydrochloric acid, heat to reflux for 6 hours, filter, concentrate under reduced pressure, cool and crystallize, refine with 130ml of concentrated hydrochloric acid, and dry to obtain 107.6g of white crystals of 3-pyridineacetic acid hydrochloride , The yield is 86%.

Example Embodiment

[0025] Example 2

[0026] a) Preparation steps of 3-pyridinethioacetylmorpholine

[0027] Add 86.8g of 3-vinylpyridine to 79g of morpholine, add 29g of sulfur while stirring, heat and reflux for reaction for 14 hours, pour the reactant into ice water and filter, wash the crystals with ice water, and dry naturally in the air to get light yellow 165 g of crystal, 90% yield.

[0028] b) Preparation steps of 3-pyridineacetic acid hydrochloride

[0029] Mix 160.2g of 3-pyridinethioacetylmorpholine with 182ml of hydrochloric acid, heat to reflux for 5 hours, filter, concentrate under reduced pressure, cool and crystallize, refine with 110ml of concentrated hydrochloric acid, and dry to obtain 110g of white crystals of 3-pyridineacetic acid hydrochloride. The yield was 88%.

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Abstract

The invention discloses a preparation process for 3-Pyridylacetic acid hydrochloride. The 3-vinylpyridine is taken as the raw material, is reacted with the morpholine and the sulphur, and then is poured into the ice water to be filtered; the crystal is washed by ice water and is naturally dried in the air to produce the 3-pyridyi thio aeid morpholine; the 3-pyridyi thio aeid morpholine is hydrolyzed by the hydrochloric acid, after the dehydration, the 3-pyridyi thio aeid morpholine is decolored by the activated carbon, is made a pressure reduction concentration, is cooled and made a crystal precipitation to produce the 3-Pyridylacetic acid hydrochloride. The invention directly takes 3-vinylpyridine as the raw material, produces the 3-Pyridylacetic acid hydrochloride only by two steps chemical reactions, develops a new path for the preparation of 3-Pyridylacetic acid hydrochloride; moreover, the preparation process is greatly shortened, the operation is simple, the yields are above 86 percent, and the quality of the product is apparently improved.

Description

technical field [0001] The present invention relates to the synthetic method of medicine intermediate 3-pyridine acetic acid hydrochloride. Background technique [0002] 3-pyridine acetic acid hydrochloride, its chemical structure is: It is a key intermediate for the synthesis of anti-osteoporosis drug risedronate sodium. Osteoporosis is a systemic metabolic disease characterized by decreased bone mass, degeneration of bone microstructure, increased bone fragility, and susceptibility to fracture. It is called "one of the three most harmful diseases to human beings in the 21st century" by western medical experts. Risedronate sodium is a third-generation bisphosphonate bone resorption inhibitor, suitable for postmenopausal osteoporosis and osteoporosis caused by the use of corticosteroids, and can also prevent bone loss in women at high risk loose disease. It is safe, effective, well tolerated, and has good application prospects. [0003] Chinese Journal of Pharmaceutica...

Claims

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Application Information

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IPC IPC(8): C07D213/55
Inventor 雷耀辉孙福年齐建伟马兴群
Owner 潍坊祥维斯化学品有限公司
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