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
View PDF5 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of cyclen
  • Preparation method of cyclen
  • Preparation method of cyclen

Examples

Experimental program
Comparison scheme
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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap