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Ritodrine hydrochloride preparation method

A technology for ritodrine hydrochloride and preparation process, which is applied in the preparation of organic compounds, chemical instruments and methods, preparation of aminohydroxy compounds, etc., can solve problems such as high cost, poor product quality, complicated post-processing, etc. The effect of production efficiency and yield, shortened process steps, and short cycle time

Inactive Publication Date: 2011-05-18
双鹤药业(海南)有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] As can be seen from the above synthetic route, the steps of method a are repeated, and the two phenolic hydroxyl groups of intermediate 6 are protected with methyl and benzyl respectively, and two steps are required for protection and deprotection; method b improves route a, using the same Class protecting group, two-step hydrogenation to get products, but the product quality is not good; method c is on the basis of route b, the first step hydrogenation reduction uses sodium borohydride, to ritodrine hydrochloride, 2-bromo-1 - p-benzyloxypropiophenone (1), synthesized through 4 steps of acylation, rearrangement, etherification and bromination, with many synthetic steps and complex post-treatment; raw material α-bromo-p-methoxyl used in method d Propiophenone is obtained by para-propionylation of anisole to obtain 4-methoxypropiophenone, and then brominated. The steps are relatively simple compared with the other three methods, but more equipment is used and the cost is high.

Method used

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  • Ritodrine hydrochloride preparation method
  • Ritodrine hydrochloride preparation method
  • Ritodrine hydrochloride preparation method

Examples

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Embodiment 1

[0034] According to the preparation method of the ritodrine hydrochloride of the present embodiment, it comprises the following steps successively:

[0035] (1) Dissolve 4-methoxypropiophenone in acetone (add a small amount of aluminum trichloride), slowly add bromine under stirring at 5°C, stir for 1.5 hours, evaporate the solvent; add p-methoxypropiophenone to the residue Ethanol solution of phenethylamine and triethylamine, reflux reaction; after the reaction, mix with 48% hydrobromic acid, then reflux reaction for 5h~8h, adjust the pH value with saturated sodium carbonate, extract the reaction solution with dichloromethane; evaporate Dichloromethane, add absolute ethanol and sodium borohydride to the residue, and reflux for 1.5h to 2h; distill off the ethanol, add an appropriate amount of water, extract with dichloromethane, distill off the dichloromethane to obtain white solid ritodrine;

[0036] (2) Add ritodrine to ethanol, slowly add concentrated hydrochloric acid drop...

Embodiment 2

[0038] According to the preparation method of the ritodrine hydrochloride of the present embodiment, it comprises the following steps successively:

[0039] (1) Dissolve 4-methoxypropiophenone in ether (add a small amount of aluminum trichloride), slowly add bromine under stirring at 5°C, stir and react for 2 hours, evaporate the solvent; add p-methoxyl to the residue The ethanol solution of phenethylamine and triethylamine, reflux reaction; after the reaction is completed, mix with 48% hydrobromic acid, and then reflux reaction for 5h-8h, adjust the pH value with saturated sodium bicarbonate solution, and extract the reaction solution with dichloromethane; Evaporate dichloromethane, add absolute ethanol and potassium borohydride to the residue, and reflux for 1.5h to 2h; distill off ethanol, add an appropriate amount of water, extract with dichloromethane, distill off dichloromethane to obtain white solid ritodrine;

[0040] (2) Add ritodrine to ethanol, slowly add concentrat...

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Abstract

The invention relates to a ritodrine hydrochloride preparation method which comprises the following steps: using 4-methoxyphenylacetone as a raw material to react with liquid bromine so as to finish alpha-site bromization; then, reacting with methoxyphenylethylamine; and carrying out hydroxylation and hydroboration, and reducing to obtain the ritodrine hydrochloride product. By combining bromization, reaction with para-methoxyphenylethylamine and hydroxylation together, the invention realizes that intermediate steps do not need to be subjected to post treatment, thereby shortening processing steps to be adapted to industrial production. The ritodrine hydrochloride preparation method has the advantages of short period and low cost, and is convenient to operate, thereby greatly improving the production efficiency and yield.

Description

technical field [0001] The invention relates to the technical field of synthesis of an anti-preterm drug ritodrine hydrochloride. Background technique [0002] Ritodrine hydrochloride, also known as hydroxybenzylhydroxyephedrine, has a chemical name of p-hydroxy-α-[1-[(p-hydroxyphenylethyl)amino]ethyl]benzyl alcohol hydrochloride. Modern pharmacological studies have shown that ritodrine is a β-sympathomimetic drug and belongs to the adrenergic β 2 Receptor agonist, its main action site is with β on uterine smooth muscle cell membrane 2 Receptor binding, activation of adenylyl cyclase, increase of intracellular cAMP concentration, reduction of intracellular free calcium concentration, relaxation of uterine smooth muscle. Due to its definite curative effect, the drug is the only fetus-preserving drug approved by the US FDA. Its half-life is between 1.5-2.5h, and the effect is faster. It can be used as an effective tocolytic to prevent the occurrence of premature labor. Ri...

Claims

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Application Information

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IPC IPC(8): C07C215/60C07C213/00
Inventor 魏雪纹李强袁芳
Owner 双鹤药业(海南)有限责任公司
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