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Method for preparing cyclen

A ring ring and dihaloethane technology, applied in the field of chemical synthesis, can solve the problems of difficult separation, many reaction steps, and low yield, and achieve the effects of cheap and easy-to-obtain raw materials, simple operation, and high yield

Inactive Publication Date: 2019-07-23
ZHEJIANG HAIZHOU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method synthesizes Luhuan Tengning, which has many steps, is not easy to separate, and has low yield
There are many three wastes, and the separation of products is difficult, which is not conducive to industrial production
[0004] At present, the synthesis method of Luhuan Tengning is to use triethylenetetramine as raw material, which involves protection and deprotection, many reaction steps, a lot of waste water and waste gas, repetitive work, and poor atom utilization rate, less than 20%.

Method used

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  • Method for preparing cyclen
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  • Method for preparing cyclen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of Lunhuan Tengning

[0021] In the reactor of 500mL, add the ethanol of 200mL, ethylenediamine 62g (1.03mol), 188g (1mol) of 1,2-dibromoethane, tetrabutylammonium bromide 6.45g (0.02mol), turn on stirring, The temperature was raised to 80°C, and the reaction was maintained for 8h. After cooling to 40°C, 20wt% liquid caustic soda was added dropwise to neutralize to pH=7-8, and the temperature was further lowered to 10-15°C for cooling and crystallization to obtain the crude product of Lunhuan Tengning. The crude product was recrystallized with 2 times the weight of ethanol to obtain 68 g of the finished product of Lunhuan Tengning, HPLC≥99%, and the yield was 79%.

[0022] The infrared absorption spectrum of the finished product of Lunhuan Tengning prepared in this example is as follows: figure 1 The NMR spectrum is shown as figure 2 shown.

Embodiment 2

[0023] Example 2: Preparation of Lunhuan Tengning

[0024] In the reaction kettle of 500mL, add the ethanol of 200mL, ethylenediamine 62g (1.03mol), 188g (1mol) of 1,2-dibromoethane, tetrabutylammonium iodide 7.4g (0.02mol), turn on stirring, The temperature was raised to 80°C, and the reaction was maintained for 8h. After cooling to 40°C, 20wt% liquid caustic soda was added dropwise to neutralize to pH=7-8, and the temperature was further lowered to 10-15°C for cooling and crystallization to obtain the crude product of Lunhuan Tengning. The crude product was recrystallized with 2 times the weight of ethanol to obtain 73.1 g of the finished product of Lunhuan Tengning, HPLC≥99%, and the yield was 85%.

Embodiment 3

[0025] Example 3: Preparation of Lunhuan Tengning

[0026] In the reactor of 500mL, add the ethanol of 200mL, ethylenediamine 62g (1.03mol), 188g (1mol) of 1,2-dibromoethane, tetrabutylammonium chloride 6g (0.0216mol), open stirring, heat up To 80 ° C, the reaction was incubated for 8 h. After cooling to 40°C, 20wt% liquid caustic soda was added dropwise to neutralize to pH=7-8, and the temperature was further lowered to 10-15°C for cooling and crystallization to obtain the crude product of Lunhuan Tengning. The crude product was recrystallized with 2 times the weight of ethanol to obtain 62 g of the finished product of Lunhuan Tengning, HPLC≥99%, and the yield was 72.1%.

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Abstract

The invention discloses a method for preparing cyclen. A reaction is carried out in a solvent by using ethylenediamine and dihaloethane as raw materials, a phase transfer reagent as a catalyst and cyclen generated by a reaction as an acid binding agent. The cyclen is obtained by treatment after the reaction is completed. The preparation of the cyclen by the method of the invention has the advantages of cheap and easily available raw materials, high yield, small pollution and simple operation, and overcomes the problems of the prior art that other acid binding agents are added for reaction, protection groups are required, and deprotection is carried out after the reaction is completed, and the protection and deprotection are complicated in process, low in yield, large in pollution and low in atomic utilization rate and the like.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for preparing Lunhuan Tengning. Background technique [0002] Lunhuan Tengning is a new generation of contrast agent, which can also be used to treat leukopenia and aplastic anemia. Due to the advantages of high activity and strong efficacy, Luhuan Tengning has more and more clinical applications and has good research value. [0003] There are mainly two preparation methods for Lunhuan Tengning. The first one: Triethylenetetramine reacts with glyoxal to protect, and then reacts with dibromoethane to deprotect, form salt, and neutralize to obtain the product. This method for synthesizing Lunhuan Tengning has many steps, is not easy to separate and has a low yield. There are many three wastes, and the separation of products has certain difficulties, which is not conducive to industrial production. The second type: Triethylenetetramine reacts with p-toluenesu...

Claims

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Application Information

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IPC IPC(8): C07D257/02
CPCC07B2200/13C07D257/02
Inventor 王俊华虞选旺冉波林远强段香江赵旭周攀虹
Owner ZHEJIANG HAIZHOU PHARMA CO LTD
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