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N-deuterium methylamine compound and preparation method thereof

A technology of amine compounds and deuteromethylamine, applied in the field of N-deuteromethylamine compounds and their preparation, can solve the problems of low selectivity, high cost, high toxicity of deuteromethylation reagents, etc. High efficiency, reduce pollution and waste, avoid the effect of highly toxic reagents and highly dangerous reagents

Pending Publication Date: 2020-06-19
SHENZHEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a kind of N-deuteromethylamine compound and its preparation method, aiming to solve the existing preparation N-deuteromethylamine reaction needs to use high temperature, high pressure condition, Low selectivity, high toxicity of deuterium methylation reagents and high cost

Method used

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  • N-deuterium methylamine compound and preparation method thereof
  • N-deuterium methylamine compound and preparation method thereof
  • N-deuterium methylamine compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0049]

[0050] Weigh 0.3mmol of p-methylaniline and 10.0mg of Pd / PCN photocatalyst into a 5mL reaction flask, and add a mixed solution of deuterium water / deuterated methanol (1.5mL / 1.5mL) to replace the reaction system with argon Protected state, then place the reaction bottle under a 420nm light source for light reaction for 4 hours, remove the light source after the reaction, and dilute the reaction mixture with 5.0mL CH 2 Cl 2 After extraction, the extract was dried over anhydrous sodium sulfate and concentrated to obtain a colorless liquid. The solvent is removed by rotary evaporation, and then the pure target product is obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether), such as Figure 1-2 shown by 1 HNMR, C-NMR and other tests confirm the structure, the yield is 89%, and the deuteration rate is >97%.

Embodiment 2

[0052]

[0053] Weigh 0.3mmol of p-methylaniline and 10.0mg of Pd / PCN photocatalyst into a 5mL reaction bottle, and add a mixed solution of water / deuterated methanol (1.5mL / 1.5mL) to replace the reaction system with argon protection state, then place the reaction bottle under a 420nm light source for 4 hours of light reaction, remove the light source after the reaction, and dilute the reaction mixture with 5.0mL CH 2 Cl 2 After extraction, the extract was dried over anhydrous sodium sulfate and concentrated to obtain a colorless liquid. The solvent is removed by rotary evaporation, and then the pure target product is obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether). 1 HNMR, C-NMR and other tests confirm the structure, the yield is 91%, and the deuteration rate is >99%.

Embodiment 3

[0055]

[0056] Weigh 0.3mmol of p-methylaniline and 10.0mg of Pd / PCN photocatalyst into a 5mL reaction bottle, and add a mixed solution of deuterium water / methanol (1.5mL / 1.5mL) to replace the reaction system with argon protection state , and then the reaction bottle was placed under a 420nm light source for 4 hours of light reaction. After the reaction, the light source was removed, and the reaction mixture was washed with 5.0mL CH 2 Cl 2 After extraction, the extract was dried over anhydrous sodium sulfate and concentrated to obtain a colorless liquid. The solvent is removed by rotary evaporation, and then the pure target product is obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether). 1 HNMR, C-NMR and other tests confirm the structure, the yield is 91%, and the deuteration rate is >99%.

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Abstract

The invnetion discloses an N-deuterium methylamine compound and a preparation method thereof. The preparation method comprises the following steps: mixing an amine compound, a deuterium source and a photocatalyst, and carrying out a reaction in an inert gas atmosphere under a light source to obtain the N-deuterium methylamine compound. According to the preparation method, more environment-friendlyand cheap deuterium water and deuterated methanol are used as deuterium sources, the deuterated methanol is used as a deuterium methyl source, and selective N-deuterium methylation reaction of the amine compound at normal temperature and normal pressure is realized by using a photocatalyst under the action of photocatalysis, so that the N-deuterium methylamine compound is prepared. Compared withthe traditional synthesis of alkylamine deuterated products, the method has the advantages of higher selectivity, milder reaction conditions and higher economic applicability.

Description

technical field [0001] The invention relates to the technical field of synthesis of deuterated compounds, in particular to an N-deuteromethylamine compound and a preparation method thereof. Background technique [0002] Deuterium is a hydrogen isotope, non-toxic, non-radioactive, and safe to the human body. Due to the isotope effect, the C-D bond is more stable than the C-H bond. Therefore, after replacing the hydrogen at a specific position in the drug with deuterium, it can block drug metabolism. site, prolonging the half-life of the drug without affecting the pharmacological activity. In 2017, as the world's first deuterated drug SD-809 (deuterated tetrabenazine) was approved for marketing in the United States, the development and application of deuterated drugs have attracted more and more attention. N-deuteromethyl drugs are one of the important components. [0003] At present, there are two methods for synthesizing N-deuteromethylamines: (1) the traditional method fo...

Claims

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Application Information

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IPC IPC(8): C07C209/68C07C209/86C07C209/84C07C211/45C07C211/55C07C253/30C07C253/34C07C255/58C07C213/08C07C213/10C07C217/84C07C211/52C07C227/16C07C227/40C07C229/60C07C211/58C07D223/22C07D223/28C07C211/30C07C211/27C07B59/00
CPCC07C209/68C07C209/86C07C209/84C07C211/45C07C211/55C07C253/30C07C253/34C07C255/58C07C213/08C07C213/10C07C217/84C07C211/52C07C227/16C07C227/40C07C229/60C07C211/58C07D223/22C07D223/28C07C211/30C07C211/27C07B59/001C07B59/002C07B2200/05
Inventor 苏陈良邱春天张钊飞李瑛
Owner SHENZHEN UNIV
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