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Preparation method of procaine

A technology of procaine and nitrocaine, which is applied in the field of preparation of procaine by aqueous phase hydrogenation of nitrocaine, can solve complex operation procedures, low yield, low procaine yield, etc. problem, to achieve the effect of improving catalytic activity, high product yield and improving selectivity

Pending Publication Date: 2022-04-05
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 2. Ethyl chloride method: in this method, 98% chloroethanol will be used, and the condensation of chloroethyl p-nitrobenzoate and diethylamine needs high pressure equipment, and the yield is not high;
[0008] 3. Esterification iron powder reduction method: the operation process of this synthesis method is more complicated, and a large amount of iron powder is also needed, and the yield of procaine is not high

Method used

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  • Preparation method of procaine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Weigh H 2 PdCl 4 Solution 5ml (which contains the quality of Pd 0.05g), RuCl 3 Solution 2ml (the quality of which contains Ru 0.005g). Add 1g of activated carbon and 10ml of deionized water into the beaker, mix well, add dropwise 2g of 5wt% ammonium oxalate solution, and stir for 5h at 60°C (stirring rate 200 rpm); then add the above two metal ion-containing solutions dropwise at the same time, Stir at 60°C for 12h (stirring rate 200 rpm). Weigh 1.8gNa 2 CO 3 and 0.1 g of sodium borohydride were dissolved in 10 ml of water, and slowly added dropwise to the catalyst solution to make the pH reach 10, then stirred for 1 h (stirring rate 200 rpm), and ultrasonicated for 1 h (ultrasonic power 100 w). Heated in a water bath at 60°C to evaporate the moisture of the catalyst to dryness. After the water was evaporated to dryness, the catalyst was transferred to a vacuum drying oven and dried in vacuum at 60°C for 8 hours to obtain a 5%Pd-0.5%Ru / C catalyst.

[0031] Add 250...

Embodiment 2

[0035] Weigh H 2 PdCl 4 Solution 2ml (the mass containing Pd 0.01g), RuCl 3 Solution 2ml (containing 0.01g of Ru mass). Add 1g of activated carbon and 10ml of deionized water in a beaker, mix well, add dropwise 1g of 10wt% ammonium oxalate solution, and stir for 2h at 80°C (stirring rate 200 rpm); then add the above two metal ion-containing solutions dropwise at the same time, Stir at 80°C for 12h (stirring rate 200 rpm). Weigh 1.8gNa 2 CO 3 , 0.1g of sodium borohydride was dissolved in 10ml of water, and slowly added dropwise to the catalyst solution to make the pH reach 10, then stirred for 1h (stirring rate 200 rpm), and ultrasonicated for 1h (ultrasonic power 100w). Heated in a water bath at 80°C to evaporate the water in the catalyst to dryness. After the water was evaporated to dryness, the catalyst was transferred to a vacuum drying oven and dried in vacuum at 110°C for 4 hours to obtain a 1%Pd-1%Ru / C catalyst.

[0036]Add 250ml of xylene, 44g of p-nitrobenzoic ac...

Embodiment 3

[0038] Weigh H 2 PdCl 4 Solution 5ml (which contains the quality of Pd 0.05g), RuCl 3 Solution 4ml (the mass containing Ru is 0.02g), add 1g activated carbon and 10ml deionized water to the beaker, mix well, add dropwise 0.5g 10wt% ammonium oxalate solution, stir at 60°C for 2h (stirring speed 200 rpm) ; Then add the above two metal ion-containing solutions dropwise at the same time, and stir at 60°C for 12h (stirring rate 200 rpm). Weigh 1.8gNa 2 CO 3 , 0.1g of sodium borohydride was dissolved in 10mL of water, and slowly added dropwise to the catalyst solution to make the pH reach 10, then stirred for 1h (stirring rate 200 rpm), and ultrasonicated for 1h (ultrasonic power 100w). Heated in a water bath at 60°C to evaporate the moisture of the catalyst to dryness. After the moisture was evaporated to dryness, the catalyst was transferred to a vacuum drying oven and dried in vacuum at 80°C for 10 hours to obtain a 5%Pd-2%Ru / C catalyst.

[0039] Add 250ml of xylene, 44g of ...

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Abstract

The invention discloses a preparation method of procaine, which comprises the following steps: (1) sequentially adding xylene, 4-nitrobenzoic acid and N, N-diethylethanolamine in a certain proportion into a reaction container in a stirring state, controlling the temperature at 140-150 DEG C, reacting and refluxing for 12-36 hours, stopping heating, and cooling to room temperature to obtain a nitrocaine solution, extracting with a 3-10% hydrochloric acid aqueous solution to obtain an upper layer which is a xylene solution and a lower layer which is a hydrochloride aqueous solution of nitrocaine; and (2) adding a hydrochloride aqueous solution of nitrocaine into a reaction kettle, adding the supported palladium-ruthenium bimetallic catalyst, introducing hydrogen until the hydrogen pressure is 0.5-2.0 MPa, controlling the reaction temperature to be 60-100 DEG C, carrying out water-phase hydrogenation reaction, and carrying out post-treatment after full reaction to obtain procaine. The method disclosed by the invention is simple in process, green and environment-friendly, and high in product yield.

Description

(1) Technical field [0001] The invention relates to a method for preparing procaine by aqueous phase hydrogenation of nitrocaine. [0002] (2) Technical background [0003] Anesthetics play a very important role in clinical practice. Local anesthetics are a class of local anesthetics that can reversibly block the generation and transmission of sensory nerve impulses, referred to as "local anesthetics". That is, in the case of staying awake, it can reversibly cause pain loss in local tissues. The earliest local anesthetic used was the alkaloid cocaine (cocaine) proposed from the leaves of coca leaves in South America. Due to the strong toxicity and addiction of cocaine, the disadvantages of high-pressure sterilization and easy hydrolysis failure have limited its application. In order to find a more ideal local anesthetic, people began to dissect, simplify and transform the structure of cocaine. Procaine hydrochloride has another name called novocaine, and its chemical name i...

Claims

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Application Information

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IPC IPC(8): C07C227/04C07C229/60B01J23/46
CPCY02P20/584
Inventor 张群峰蒋飘飘王清涛许孝良李小年
Owner ZHEJIANG UNIV OF TECH
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