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Preparation method of oxybuprocaine hydrochloride

A technology of obucaine and nitrobenzoic acid, applied in the field of compound synthesis, can solve the problems of high equipment requirements, unfavorable production, easy combustion and explosion, etc., and achieves the effect of easy cost

Inactive Publication Date: 2017-06-09
SHENZHEN OASIS PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] (1) Use 3-hydroxy-4-nitrobenzoic acid as a raw material, react in an autoclave, and use Raney nickel as a catalyst for reduction, which is easy to burn and explode, and has high requirements for equipment, which is not conducive to production

Method used

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  • Preparation method of oxybuprocaine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1, preparation oxybucaine hydrochloride

[0040] (1) Preparation of ethyl 3-butoxy-4-nitrobenzoate

[0041] Add 40g 3-hydroxyl-4-nitrobenzoic acid ethyl ester, 31g bromobutane, 31g anhydrous potassium carbonate and 400ml DMF in the there-necked flask, in the reaction system, 3-hydroxyl-4-nitrobenzoic acid ethyl ester, bromine The molar ratio of butane to potassium carbonate is 1:1.2:1.2; heat to 80°C, react for 12 hours, after the reaction is completed, remove the solvent by rotary evaporation, add 200ml of water to the residue, stir and crystallize for 12 hours, filter to obtain 52g of light yellow Solid 3-butoxy-4-nitro-benzoic acid ethyl ester.

[0042] (2) Preparation of 3-butoxy-4-nitro-benzoic acid

[0043] Add 52g of ethyl 3-butoxy-4-nitrobenzoate obtained in step (1) and 150ml of 15wt% sodium hydroxide solution into a three-necked flask, stir, heat at 60°C, react for 1h, cool down with ice water, and slowly add hydrochloric acid , adjusted the pH t...

Embodiment 2

[0050] Embodiment 2, preparation oxybucaine hydrochloride

[0051] (1) Preparation of ethyl 3-butoxy-4-nitrobenzoate

[0052] Add 400g 3-hydroxyl-4-nitrobenzoic acid ethyl ester, 310g bromobutane, 310g anhydrous potassium carbonate and 4000ml DMF in the there-necked flask, 3-hydroxyl-4-nitrobenzoic acid ethyl ester, bromobutane and carbonic acid The molar ratio of potassium is 1:1.2:1.2; heat to 80°C, react for 14 hours, after the reaction is completed, remove the solvent by rotary evaporation, add 2000ml of water to the residue, stir and crystallize for 12 hours, filter to obtain 531g of light yellow solid 3-butyl Oxy-4-nitro-benzoic acid ethyl ester.

[0053](2) Preparation of 3-butoxy-4-nitrobenzoic acid

[0054] Add 530g of 3-butoxy-4-nitro-benzoic acid ethyl ester obtained in step (1) and 1590ml of 15wt% sodium hydroxide solution into a three-necked flask, stir, heat to 60°C, react for 1h, cool down with ice water, slowly Hydrochloric acid was added to adjust the pH to...

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Abstract

The invention discloses a preparation method of oxybuprocaine hydrochloride. The preparation method includes following steps: in the presence of alkali I, subjecting 3-hydroxy-4-ethyl nitrobenzoate and bromobutane to electrophilic substitution reaction to obtain 3-butoxy-4-ethyl nitrobenzoate; under alkaline condition, enabling 3-butoxy-4-ethyl nitrobenzoate to be in hydrolysis reaction, and adjusting pH value of a system after hydrolysis reaction to 1-3 to obtain 3-butoxy-4-nitrobenzoic acid; in the presence of alkali II, subjecting the 3-butoxy-4-nitrobenzoic acid and diethylamino ethyl chloride to electrophilic substitution reaction to obtain 4-nitro-2-butoxy nitrobenzoic acid-2-(diethylamino) ethyl ester, and subjecting the 4-nitro-2-butoxy nitrobenzoic acid-2-(diethylamino) ethyl ester to reduction reaction under action of ferric trichloride and hydrazine hydrate to obtain oxybuprocaine hydrochloride. 3-hydroxy-4-ethyl nitrobenzoate is adopted as a raw material to obtain a target product through four steps of conventional reaction; each step of reaction does not need high-pressure condition, and needed raw materials are all conventional compounds, so that the preparation method is easy to obtain and low in cost.

Description

technical field [0001] The invention relates to a preparation method of oxybucaine hydrochloride, which belongs to the field of compound synthesis. Background technique [0002] Obucaine hydrochloride has another name called butoxyprocaine hydrochloride, its chemical name is 2-(diethylamino)ethyl 4-amino-3-butoxybenzoate hydrochloride, and its structural formula is as follows Formula I As shown, it is a kind of local anesthetic, which can block the conduction of peripheral nerve endings and fibers, and temporarily lose the feeling of the corresponding tissues, thus achieving an anesthesia effect. In medical treatment, it is used for surface anesthesia, lubrication and pain relief in various examinations, treatment, and minor operations. It has effective curative effect, is safe to use, has little irritation and toxicity, and has no drug addiction. The need is huge. [0003] [0004] In the prior art, the synthetic method of oxybucaine hydrochloride mainly contains the f...

Claims

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Application Information

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IPC IPC(8): C07C227/04C07C229/64
CPCC07C227/04C07C201/12C07C213/00C07C229/64C07C219/14C07C205/59
Inventor 赖福平
Owner SHENZHEN OASIS PHARMA
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