Synthetic process of hydrochloric acid trientine

A hydrochloric acid and new process technology, applied in the preparation of amino compounds, the preparation of organic compounds, organic chemistry, etc., can solve the problems of difficult control of the conditions for dihydrochloride formation, and achieve the effects of easy conditions, easy operation and little pollution

Inactive Publication Date: 2013-02-13
GUANGDONG AOERCHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since tetrahydrochloride is more stable than dihydrochloride, the literature uses excess hydrogen chloride to form salt, and the conditions for forming dihydrochloride are difficult to control
Meanwhile, the synthetic methods reported in the above literatures involve the use of highly toxic compounds such as potassium cyanide

Method used

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  • Synthetic process of hydrochloric acid trientine
  • Synthetic process of hydrochloric acid trientine
  • Synthetic process of hydrochloric acid trientine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1) Preparation of Intermediate B:

[0037] The molar ratio of starting material A: absolute ethanol: 80% hydrazine hydrate is 1:275:7.8.

[0038] Preparation method: Add 276g of starting material A: 2,2'-(2,2'-(ethane-1,2-diyl -Bisbenzyl-bis(ethane-2,1-diyl))diisoindole-1,3-dione, 7.5L absolute ethanol, 230mL80% hydrazine hydrate, heated to 60-70°C under stirring, React for 18 hours, stir and cool to room temperature, continue to stir for 2 hours, filter with suction, wash the filter residue with absolute ethanol, concentrate the mother liquor on a rotary evaporator until there is no distillate, and reclaim ethanol. Add appropriate amount of anhydrous to the solid in the bottle Ethanol, stirred, suction filtered, and the filter residue was washed with a small amount of absolute ethanol. The combined filtrate was concentrated to dryness under reduced pressure on a rotary evaporator to obtain a yellow oil, which was Intermediate B: N1, N1'-(B alkane-1,2-diyl)bis(N1-benz...

Embodiment 2

[0051] 1) Preparation of Intermediate B:

[0052] The molar ratio of starting material A: absolute ethanol: 60% hydrazine hydrate is 1:270:10.

[0053]Preparation method: Add 276g of starting material A: 2,2'-(2,2'-(ethane-1,2-diyl -Bisbenzyl-bis(ethane-2,1-diyl))diisoindole-1,3-dione, 7.0L absolute ethanol, 390mL60% hydrazine hydrate, heated to 60-70°C under stirring, React for 20 hours, stir and cool to room temperature, continue to stir for 2 hours, filter with suction, wash the filter residue with absolute ethanol, concentrate the mother liquor on a rotary evaporator until there is no distillate, and recover ethanol. Add appropriate amount of anhydrous to the solid in the bottle Ethanol, stirred, suction filtered, and the filter residue was washed with a small amount of absolute ethanol. The combined filtrate was concentrated to dryness under reduced pressure on a rotary evaporator to obtain a yellow oil, which was Intermediate B: N1, N1'-(B alk-1,2-yl)bis(N1-benzylethan...

Embodiment 3

[0062] 1) Preparation of Intermediate B:

[0063] The molar ratio of starting material A: absolute ethanol: 70% hydrazine hydrate is 1:300:7.

[0064] Preparation method: Add 276g of starting material A: 2,2'-(2,2'-(ethane-1,2-diyl -Bisbenzyl-bis(ethane-2,1-diyl))diisoindole-1,3-dione, 8.3L absolute ethanol, 235mL70% hydrazine hydrate, heated to 60-70°C under stirring, React for 15 hours, stir and cool to room temperature, continue to stir for 2 hours, filter with suction, wash the filter residue with absolute ethanol, concentrate the mother liquor on a rotary evaporator until there is no distillate, and reclaim ethanol. Add appropriate amount of anhydrous to the solid in the bottle Ethanol, stirred, suction filtered, and the filter residue was washed with a small amount of absolute ethanol. The combined filtrates were concentrated to dryness on a rotary evaporator under reduced pressure to obtain a yellow oil, which was Intermediate B.

[0065] 2) Preparation of Intermediat...

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Abstract

The invention discloses a novel synthetic process of hydrochloric acid trientine, and aims at providing the synthetic method of the hydrochloric acid trientine. The synthetic process can avoid using a highly-toxic material, namely potassium cyanide, and is temperate in reaction condition. A compound 2,2'-(2,2'-(ethane-1,2-diradical-bibenzyl-di (ethane-2,1-double radical)) bi isoindole-1,3-diketone is used as an initiator, after hydrazinolysis, an intermediate N1, N1'-(ethane-1,2-diradical) di(N1-nethyl ethane-1,2-diamine) is obtained. Through carbobenzoxy protection (Cbz protection), salt is generated,and dibenzyl 2,2'-(ethane-1,2-diradical-di (benzylamine-diradical)) di (ethane-2,1-diradical) dioctyl phthalatic acid aster hydrochloride is obtained so as to crystallize in ethanol through pressing catalytic hydrogenation deprotection to directly obtain the hydrochloric acid trientine. The synthetic process belongs to the organic synthetic technical field.

Description

technical field [0001] The invention discloses a synthesis process, in particular to a synthesis process of trientine hydrochloride; it belongs to the technical field of organic synthesis. Background technique [0002] Regarding the synthesis of triethylenetetramine, there are many patents and literature reports, such as: US4806519; US4550209; US4766247; EP450709; RU2186761; However, the methods reported in the above literature often require higher temperature and pressure, and the purity of the product is also difficult to control. US2010 / 0172994A1 reported a new method for synthesizing triethylenetetramine and its salts under mild conditions. The synthetic route is as follows: [0003] Route 1: [0004] [0005] Route two: [0006] [0007] The active ingredient of trientine as a bulk drug is triethylenetetramine dihydrochloride. In the above-mentioned documents, trientine tetrasalt is first synthesized, then alkalized into free base, and triethylenetetramine di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/14C07C209/62
Inventor 吴智南陈小坚招翠微周小忠钟瑜
Owner GUANGDONG AOERCHENG PHARMA
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