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Method for synthesizing benzyloxy amine hydrochloride

A technology for synthesizing benzyloxyamine hydrochloride and synthetic routes, which is applied in the field of synthesis of benzyloxyamine hydrochloride, can solve the problems of increased difficulty of synthesis, decreased reaction yield, high reagent cost, etc., and achieves low cost and mild conditions , The effect of simple operation

Inactive Publication Date: 2004-04-14
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The disadvantage of this reaction is that the yield of the reaction is very low, less than 5%
[0020] Whether it is to select complex large protecting groups or diethyl azodicarbonate (DEAD) or diisopropyl azodicarbonate (DIAD) used in the Mitsunobu reaction, the cost of the reagent is high, and it needs to be stored at low temperature, which increases the The difficulty of mass synthesis
Not only that, anaerobic conditions must be ensured in the reaction, otherwise, the light reaction yield will decrease, and the severe one will explode, which is difficult to control in industry

Method used

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  • Method for synthesizing benzyloxy amine hydrochloride
  • Method for synthesizing benzyloxy amine hydrochloride
  • Method for synthesizing benzyloxy amine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Step 1 Synthesis of free hydroxylamine

[0037]

[0038] Weigh hydroxylamine hydrochloride (403mg, 5.8mmol), add ethanol 1.3mL and stir at room temperature to completely dissolve hydroxylamine hydrochloride. Sodium hydroxide (725mg, 18.1mmol) aqueous solution (0.3mL) was slowly added in batches, and the reaction temperature was controlled at 25-40°C. After the addition of alkali, the reaction system was naturally stirred and cooled to room temperature for 0.5h. The next reaction was carried out directly without separation.

[0039] Step 2 synthesis of hydroxylamine acetone oxime 2

[0040]

[0041] Acetone (0.3mL) was added dropwise with a dropping funnel. The acetone was exothermic violently and cooled in an ice bath. Meanwhile, the reaction temperature was controlled at 0-60°C by controlling the rate of acetone addition. After the reaction was stable, it was reacted at room temperature for 15 hours. Extract with ether, wash the combined organic phase wi...

Embodiment 2

[0049] Step 1 Release free hydroxylamine

[0050] Hydroxylamine was prepared from compound 1 according to the method of Example 1.

[0051] Hydroxylamine hydrochloride (10.0 g, 144 mmol) was weighed in a double-necked flask equipped with a dropping funnel, 15 mL of water was added into the double-necked flask, and the hydroxylamine hydrochloride was completely dissolved by stirring at room temperature. Potassium hydroxide (8.9g, 158mmol) was slowly added in batches in an ice bath. After adding the base, the reaction temperature was controlled not to exceed 50°C. After 5h, the reaction system was cooled to room temperature, and the next reaction was carried out directly.

[0052] Step 2 synthesis of hydroxylamine acetone oxime 2

[0053] Hydroxyamine acetone oxime is prepared by the method of embodiment 1 by hydroxylamine.

[0054] Acetone (14mL) was added dropwise with a dropping funnel. When acetone was added, the heat was exothermic violently. The reaction temperature was ...

Embodiment 3

[0061] Step 1 Synthesis of free hydroxylamine

[0062] Hydroxylamine was prepared from compound 1 according to the method of Example 1.

[0063] Step 2 synthesis of hydroxylamine acetone oxime 2

[0064] Hydroxyamine acetone oxime is prepared by the method of embodiment 2 by hydroxylamine.

[0065] Step 3 Synthesis of benzyloxyamine acetone oxime 3

[0066] According to the method of Example 1, benzyloxyamine acetone oxime was prepared from compound 2.

[0067] Weigh NaH (1.9g, 82mmol), under nitrogen atmosphere, wash off the mineral oil on the surface of sodium hydrogen with dry tetrahydrofuran, add DMF (200mL) after washing, cool with ice-water bath, add dropwise hydroxylamine acetone oxime ( 5g, 68.5mmol) in DMF (50ml), continue to react at 0°C for 0.5h after the dropwise addition until there is no obvious bubbling. Benzyl bromide BnBr (8.2ml, 68.5mmol) was added dropwise in an ice-water bath, and the reaction continued for 5h after the addition was complete. Add satur...

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Abstract

The invention refers to a manufacturing method of an important medicine and the organic synthesis midbody-benzyl oxide amine hydrochlorate. The invention starts from hydroxylamine hydrochlorate and gets acetoxime through batching reaction. There obtains the product by the liquor hydrochloric acid under the controlled temperature. The increasing of midbody molecular is little, and the reaction efficiency is high, the whole line atom economic is good. The cost is low.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing important medicine and organic synthesis intermediate benzyloxyamine hydrochloride. (2) Background technology [0002] Benzyloxamine is unstable, but it can exist stably in the form of hydrochloride. The reason for the early synthesis of benzyloxyamine hydrochloride is that it can effectively treat tuberculosis. 5% mg of benzyloxyamine or 10% benzyloxyamine Oxyamine dissolved in bovine serum can effectively treat tuberculosis, and at the same time it can reduce blood cholesterol levels. Now benzyloxyamine, as an important drug intermediate and organic synthesis intermediate, is often used in reactions such as the introduction of hydroxylamine and oxime, and has high commercial value, so its synthesis research is still attracting attention. Although it is a widely used synthetic intermediate, it is produced by only a few large reagent companies in the world. In Asia, only Japan’s Tokyo Chemical Ind...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C291/02
Inventor 黄培强黄慧英
Owner XIAMEN UNIV
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