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Preparation method of N-diethylaminoacetyl-2,6-dimethylaniline quaternary ammonium salt

A technology of diethylaminoacetyl and dimethylaniline, applied in the field of pharmaceutical synthesis, can solve the problems of unstable raw materials, low purity, low yield and the like, and achieves a complete reaction, high yield and purity, and economical and environmentally friendly yields. Effect

Pending Publication Date: 2021-02-23
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In order to solve the problems of low yield, low purity and unstable raw materials in the preparation process of QX-314-OH in the prior art, the present invention provides a new method for preparing QX-314-OH. The preparation method is novel and the raw materials are easy to obtain , simple operation, milder reaction, economical and environmental protection and high yield, suitable for industrial production

Method used

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  • Preparation method of N-diethylaminoacetyl-2,6-dimethylaniline quaternary ammonium salt
  • Preparation method of N-diethylaminoacetyl-2,6-dimethylaniline quaternary ammonium salt
  • Preparation method of N-diethylaminoacetyl-2,6-dimethylaniline quaternary ammonium salt

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Effect test

Embodiment 1

[0027] Weigh 24.2g of 2-bromo-N-(2,6-dimethylphenyl)acetamide and add it to 100ml of acetonitrile solution, add 21.1g of diethylaminoethanol, heat to 75-80°C and stir to react, TLC detects that the reaction is complete After cooling down to room temperature to obtain solid QX-314-OH, add the obtained crude QX-314-OH to 50ml of anhydrous ether and heat to dissolve, then cool down to 20°C, keep stirring and crystallize for 3h, filter with suction, and vacuum-dry the obtained filter cake at 45°C The yield of QX-314-OH was 73.4%, and the HPLC purity was 99.56%.

Embodiment 2

[0029] Weigh 24.2g of 2-bromo-N-(2,6-dimethylphenyl)acetamide and add it to 100ml of toluene solution, add 21.1g of diethylaminoethanol, heat to 80-85°C and stir to react, TLC detects that the reaction is complete After cooling down to room temperature to obtain solid QX-314-OH, add the obtained crude QX-314-OH to 60ml of methanol for heating and dissolving, then lower the temperature to 10°C, keep stirring and crystallize for 2 hours, filter with suction, and dry the obtained filter cake under vacuum at 45°C to obtain QX -314-OH, the yield is 71.7%, and the HPLC purity is 99.48%.

Embodiment 3

[0031] Weigh 24.2g of 2-bromo-N-(2,6-dimethylphenyl)acetamide and add it to 100ml of acetonitrile solution, add 16.4g (0.14mol) of diethylaminoethanol, heat to 60-65°C and stir to react. After TLC detection, the reaction was lowered to room temperature to obtain solid QX-314-OH, and the obtained crude QX-314-OH was added to 50ml of anhydrous ether for heating and dissolving, then cooled to 25°C for 3 hours with stirring and crystallization, and filtered with suction to obtain the filter cake Vacuum drying at 45°C gave QX-314-OH with a yield of 70.5% and an HPLC purity of 99.51%.

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Abstract

The invention belongs to the technical field of medicine synthesis, and particularly relates to a preparation method of N-diethylaminoacetyl-2,6-dimethylaniline quaternary ammonium salt. The method for preparing the N-diethylaminoacetyl-2,6-dimethylaniline quaternary ammonium salt comprises the following steps of: reacting 2-bromo-N-(2,6-dimethylphenyl)acetamide serving as a raw material with diethylaminoethanol to obtain an N-diethylaminoacetyl-2,6-dimethylaniline quaternary ammonium salt crude product, and further stirring and crystallizing the crude product in an organic solvent to obtain the N-diethylaminoacetyl-2,6-dimethylaniline quaternary ammonium salt pure product. The method provided by the invention has the advantages of simple reaction conditions and simplified preparation process, effectively enhances the yield and purity of the N-diethylaminoacetyl-2,6-dimethylaniline quaternary ammonium salt, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of N-diethylaminoacetyl-2,6-dimethylaniline quaternary ammonium salt. Background technique [0002] The chemical name of N-diethylaminoacetyl-2,6-dimethylaniline quaternary ammonium salt (Acipimox) is (2-(2,6-dimethylphenylamino)-N,N-diethyl-N- (2-Hydroxyethyl)-2-oxoethylammonium bromide, referred to as QX-314-OH, QX-314 is a tetravalent cationic derivative of lidocaine, QX-314-OH is a newly synthesized QX-314 Hydroxyl compounds are quaternary ammonium local anesthetics. Compared with QX-314 at the same concentration, QX-314-OH can not only produce durable local anesthesia, but also have moderate toxicity to local tissues. Low concentration of QX-314-OH and The combination of low concentration of levobupivacaine can produce ideal analgesic effect, the structure is as follows: [0003] [0004] At present, there are relatively few r...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C237/04
CPCC07C231/12C07C237/04
Inventor 张贵民冯启国马秀玲
Owner LUNAN PHARMA GROUP CORPORATION
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