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Preparation method of cyclen and intermediate thereof

A compound, a technology of hydrazine hydrate, which is applied in the field of preparation of cyclamenine and its intermediates, and can solve the problems of single types of synthetic routes and the like

Active Publication Date: 2021-07-06
LIANHE CHEM TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] The technical problem to be solved by the present invention is to overcome the single defect of the synthetic route of the existing trichotene, and provide a preparation method of the tritane and its intermediate

Method used

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  • Preparation method of cyclen and intermediate thereof
  • Preparation method of cyclen and intermediate thereof
  • Preparation method of cyclen and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101]

[0102] Dissolve 100 g of triethylenetetramine and 163 g of benzotriazole in 400 mL of ethanol, add dropwise 200 g of 40% glyoxal aqueous solution at 0°C, stir at 0°C for 3 hours, and pass the reaction control. Add 52 g of sodium borohydride at 0°C and stir for 3 hours. After the reaction control is qualified, remove the insoluble salt by filtration, concentrate the filtrate to remove ethanol, add 600mL of toluene, heat up and carry out normal pressure reflux to divide water, after completely removing the water, cool down to 20°C, and filter to remove the insoluble solid benzotriazole ( For recovery, the recovery rate is 92%), the filter cake is washed once with 100mL toluene, the filtrate is combined, and the filtrate is concentrated under reduced pressure until no obvious fractions are distilled out to obtain 100 grams of light yellow oily matter of the compound of formula 2, with a yield of 75% , with a content of about 70%. 1 H NMR (CDCl 3 ,400MHz):3.087(s,2H)...

Embodiment 2

[0104]

[0105] 56 grams of the compound of formula 2 (according to the purity of 100%) were dissolved in 1000 mL of ethanol, cooled to 0° C., and 68.6 grams of 98% sulfuric acid was added dropwise, and stirred at 0° C. for 5 hours. After filtering, the filter cake was washed with ethanol, and the filter cake was dried to obtain 107 g of the compound of formula 3-1, with a yield of 95%. The purity of compound 3-1 is not less than 96%, total nitrogen: 14.45%.

Embodiment 3

[0107]

[0108] 56 grams of the compound of formula 2 (according to the purity of 100%) were dissolved in 1000 mL of ethanol, cooled to 0° C., and 173 grams of 98% sulfuric acid was added dropwise, and stirred at 0° C. for 5 hours. After filtering, the filter cake was washed with ethanol, and the filter cake was dried to obtain 108 g of the compound of formula 3-1, with a yield of 95%.

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Abstract

The invention discloses a preparation method of cyclen and an intermediate thereof, specifically a preparation method of a compound as shown in a formula 4. The method comprises the following step: in water, carrying out a reduction reaction as shown in the specification on a compound as shown in a formula 3 and hydrazine hydrate, wherein X is phosphoric acid or sulfuric acid, when X is phosphoric acid, n is 4 / 3, and when X is sulfuric acid, n is 2. The preparation method has the advantages of low cost, simple operation, easy purification of intermediates and products, high yield and purity, and suitableness for industrial production.

Description

technical field [0001] The invention relates to the field of chemical synthesis, and in particular to a preparation method of trigonine and its intermediate. Background technique [0002] Cyclone (1,4,7,10-tetraazadodecane, Cyclen) is a white or nearly white crystalline powder chemical. Molecular formula is C 8 h 20 N 4 , the molecular weight is 172.28. It is a very important intermediate in the synthesis of diagnostic kits and therapeutic drugs. It is used to remove stones in the human body, especially in the manufacture of contrast agents for medical imaging technologies such as nuclear magnetic resonance imaging (MRI), X-ray CT, and ultrasound imaging, as well as radiopharmaceutical treatment of malignant tumors. It shows extremely important application value. As a precursor of a macrocyclic chelating agent for synthesizing metal ions, it can form very stable complexes with ions, especially paramagnetic metal ions, such as the complexes formed with gadolinium ions a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/02C07D487/22
CPCC07D257/02C07D487/22
Inventor 张锴谢四维李永锋邹本立
Owner LIANHE CHEM TECH
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