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Preparation method of cyclen

A technology for the preparation of cylindrine and its intermediates, which can solve the problems of easy decomposition, many side reactions, and unfavorable scale-up production, and achieve good reaction selectivity, reduced production costs, and high reaction yield. Considerable effect

Inactive Publication Date: 2020-01-17
CHEN STONE GUANGZHOU CO LTD
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Problems solved by technology

[0015] The diethyl oxalate method has simple and easy-to-obtain raw materials, few steps, and mild conditions, but the two-step yields are 39% and 56% respectively, and diborane is unstable, easy to decompose when wet, and explode, so it is not suitable for large-scale production
[0016] The laboratory production effect of the Dow route method is better, but the solvent used is expensive, easy to absorb water, has many side reactions, and the amplification yield is greatly reduced

Method used

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Experimental program
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Effect test

Embodiment

[0045] Step 1: Refining of TETA

[0046]

[0047] Add 1.0kg of triethylenetetramine (TETA) and 0.17kg of water into the reaction vessel, control the temperature at 20-50°C, add a small amount of seed crystals, then add 1.5-2.0kg of toluene dropwise, and control the temperature at 20-50°C, drop After completion, lower the temperature to 0-20° C., and keep stirring for 2-4 hours, then filter, collect the filter cake, and obtain 850 g after drying, with a purity of 99%.

[0048] 1 H-NMR (400MHz, CDCl 3 ,ppm)δ:2.92(s,4H),2.56(m,12H),2.49(m,6H).

[0049] The second step: the preparation of intermediate 2

[0050]

[0051] Add 350g of compound 1 into the reaction vessel, add 3~4L of absolute ethanol, cool down to -10~5°C, under nitrogen atmosphere, add dropwise a solution of 40% aceguvaldehyde (347~520g) in ethanol (1.5~2.0L), keep warm After stirring for 2-4 hours, TLC monitored the completion of the reaction, and the product was directly used in the next reaction without...

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Abstract

The invention provides a preparation method of cyclen. The method comprises the following step: taking triethylenetetramine (TETA) as a raw material to carry out refining, then carrying out a reactionon the refined triethylenetetramine with methylglyoxal to obtain an intermediate 2, carrying out cyclization on the intermediate 2 with glyoxal, carrying out reducing with sodium borohydride to obtain a cyclized intermediate 3, finally carrying out ring opening through acid hydrolysis, and then adjusting the pH value by using an alkali solution to free out the cyclen.

Description

technical field [0001] The present invention relates to a kind of preparation method of trigonine. Background technique [0002] Cyclone (1,4,7,10-tetraazacyclododecane, cyclen) is a very important intermediate in the synthesis of diagnostic kits and therapeutic drugs. It is used to remove stones in the human body and inhibit the loss caused by myocardial ischemia-reperfusion, especially in the manufacture of contrast agents for medical imaging technologies such as magnetic resonance imaging (MRI), X-ray CT, and ultrasound imaging, as well as radiotherapy drugs for malignant tumors On the one hand, trachine and its derivatives have shown extremely important application value. As the precursor of the macrocyclic chelating agent for synthesizing metal ions, it can form very stable complexes with ions, especially with paramagnetic metal ions, such as the complexes formed with gadolinium ions, which are used in the field of medical diagnosis. There will be high toxicity caused...

Claims

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Application Information

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IPC IPC(8): C07D257/02
CPCC07D257/02
Inventor 梁龙赖英杰夏学良王绪炎黄申振
Owner CHEN STONE GUANGZHOU CO LTD
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