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Method for preparing 5-(N,N-dibenzylglycyl) salicylamide

A technology of dibenzylaminoacetyl and acetylsalicylic amide, applied in the field of preparation of 5-salicylic amide, can solve problems such as inability to satisfy, and achieve the effects of low product cost, convenient and abundant sources, and low impurity content

Inactive Publication Date: 2009-10-21
JIANDE ZISHANWAN FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Obviously, above technique can't meet the high requirement of labetalol hydrochloride production to 5-(N, N-dibenzylaminoacetyl) salicylamide quality and cost
[0014] Invention application CN200810155046 discloses a method for preparing acetylsalicylamide, specifically referring to the use of triethylammonium aluminum trichloride (C 2 h 5 ) 3 NHCL-NALCL 3 (N=2.0~2.5) ionic liquid is catalyst and solvent, the new method that catalyzes salicylamide acylation prepares acetylsalicylic amide, specifically under nitrogen protection when reactant salicylamide temperature rises to 32- in ionic liquid At 46°C, acetyl chloride is added for reaction synthesis, but one of the methods only involves the preparation of 5-(N, N-dibenzylaminoacetyl) salicylamide intermediate acetyl salicylamide, and the other, this method is the same as this method The preparation method of the intermediate of the invention application is completely different

Method used

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  • Method for preparing 5-(N,N-dibenzylglycyl) salicylamide
  • Method for preparing 5-(N,N-dibenzylglycyl) salicylamide
  • Method for preparing 5-(N,N-dibenzylglycyl) salicylamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Under normal pressure, put 800 kg of methanol and 400 kg of water into the amination kettle, put in 258 kg of 5-BrASA product, cool and control the temperature below 40°C, add dropwise a mixed liquid of 405 kg of dibenzylamine and 400 kg of methanol, and reflux at 65°C After 2 hours, cool to room temperature and centrifuge to obtain crude 5-DNSA, and the mother liquor obtained by centrifugation can be distilled to recover methanol and dibenzylamine. Put the crude product into the refining kettle, then put in 1000 kilograms of ethyl acetate, and then heat up the steam at 75° C. and reflux for 5 hours, then cool to normal temperature, and vacuum-dry at 100° C. after centrifugation to obtain 305 kilograms of 5-DNSA product (yield 85%). Ethyl acetate was recovered by distillation. The 5-DNSA product obtained in this example has a white powder appearance. After testing, its m.p. acid 0.05%, methyl 5-(N,N-dibenzylaminoacetyl)salicylate 0.02%.

Embodiment 2

[0081] Under normal pressure, put 800 kg of methanol and 500 kg of water into the amination kettle, put in 258 kg of 5-BrASA product, cool and control the temperature below 30°C, add dropwise a mixed liquid of 440 kg of dibenzylamine and 400 kg of methanol, and reflux at 65°C After 2 hours, cool to room temperature and centrifuge to obtain crude 5-DNSA, and the mother liquor obtained by centrifugation can be distilled to recover methanol and dibenzylamine. Put the crude product into the refining kettle, then put in 1000 kg of ethyl acetate, and then heat up the steam at 75° C. and reflux for 3 hours, then cool to normal temperature, and vacuum dry at 100° C. after centrifugation to obtain 320 kg of 5-DNSA product (yield 90%). Ethyl acetate was recovered by distillation. The 5-DNSA product obtained in this example has a white powder appearance. After testing, its m.p. Acid content was 0.07%, methyl 5-(N,N-dibenzylaminoacetyl) salicylate was 0.02%.

Embodiment 3

[0083] Under normal pressure, put 800 kg of methanol and 450 kg of water into the amination kettle, put 258 kg of 5-BrASA product into it, cool and control the temperature below 30°C, add dropwise a mixed liquid of 420 kg of dibenzylamine and 400 kg of methanol, and reflux at 65°C After 3 hours, cool to room temperature and centrifuge to obtain crude 5-DNSA, and the centrifuged mother liquor can be distilled to recover methanol and dibenzylamine. Put the crude product into the refining kettle, then put in 1000 kilograms of ethyl acetate, and then heat up the steam at 75° C. and reflux for 5 hours, then cool to normal temperature, and vacuum-dry at 100° C. after centrifugation to obtain 314 kilograms (yield 88%) of 5-DNSA product. Ethyl acetate was recovered by distillation. The 5-DNSA product obtained in this example has a white powder appearance. After testing, its m.p. Acid content was 0.06%, and methyl 5-(N,N-dibenzylaminoacetyl)salicylate was 0.01%.

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Abstract

The invention belongs to the field of medical intermediate, and particularly discloses a method for preparing a 5-(N,N-dibenzylglycyl) salicylamide. The method comprises the following steps of mixing dibenzylamine and 5-(bromoacetyl) salicylamide with the molar ratio more than or equal to 2 and taking carbinol and water as solvent so as to react under the circumfluence condition at the temperature less than or equal to 40 DEG C; obtaining a coarse product by centrifuging the reaction products, and refining the coarse product by ethyl acetate, thus obtaining the 5-(N,N-dibenzylglycyl) salicylamide. The method has the advantages of simple preparation method, easy industrial production, high product yield, high purity, etc.

Description

technical field [0001] The invention relates to the field of pharmaceutical intermediates, in particular to a preparation method of 5-(N,N-dibenzylaminoacetyl) salicylamide. Background technique [0002] 5-(N,N-dibenzylaminoacetyl) salicylamide is an important intermediate in the manufacture of cardiovascular drug labetalol hydrochloride (saladol). [0003] Labetalol hydrochloride is an antihypertensive drug with α and β receptor blocking effects. It is the first representative drug that simultaneously blocks α and β receptors in clinical application. It has become one of the antihypertensive drugs widely used in European and American countries because of its strong and definite curative effect. Once the drug came out, it was rapidly promoted in countries all over the world. The drug is suitable for all kinds of high blood pressure, especially safe and effective for hypertensive crisis. It is also suitable for high blood pressure with coronary heart disease and high blood p...

Claims

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Application Information

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IPC IPC(8): C07C237/30C07C231/12
Inventor 钟朝康
Owner JIANDE ZISHANWAN FINE CHEM
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