Preparation method of amide

An amide, selected technology, applied in the field of amide preparation, can solve problems such as complexity, long reaction steps, and reduced economy, and achieve the effects of reducing reaction steps, improving utilization rate, and reducing costs

Inactive Publication Date: 2013-05-22
JINAN ZHIHE MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] In the reaction of preparing the final product by the above method, the precursor must be further reacted with propionyl chloride to prepare the final product, so the reaction steps are long and complicated, and the economy is reduced

Method used

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  • Preparation method of amide
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  • Preparation method of amide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Preparation of compound 1 (tasimelteon)

[0045] (compound 1)

[0046](1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropylcarboxamide ( ), (the starting reactant can be prepared according to the method disclosed in Chinese patent application CN102675268A), 1.9g of sodium borohydride is added in 40ml of anhydrous tetrahydrofuran, heated to reflux, wherein (1R,2R)-2-(2,3 The mol ratio of -dihydrobenzofuran-4-yl)cyclopropylcarboxamide and sodium borohydride is about 1:5, slowly add dropwise the mixed solution of 12.5g propionic acid and 20ml anhydrous tetrahydrofuran (sodium borohydride and propionic acid The molar ratio is about 1:3.3), the addition is completed in 12 hours, and then the reaction is continued at 70°C for about 6 hours, down to room temperature, the material is slowly poured into 100ml of ice water, and about 20g of hydrochloric acid with a mass concentration of 10% is added dropwise while stirring , adjust the pH value to about 2. The obtain...

Embodiment 2

[0048] Example 2: Preparation of Compound 2 (Rimeteon)

[0049] (Compound 2)

[0050] 3.2g of the compound As the starting reactant (the starting reactant can be prepared according to the preparation method described in the patent JP11080106), 1.9 g of sodium borohydride is added to 40 ml of anhydrous tetrahydrofuran, and heated to reflux, wherein the mole of the starting reactant and sodium borohydride The ratio is about 1:5, slowly add a mixed solution of 12.5g propionic acid and 20ml anhydrous tetrahydrofuran (the molar ratio of sodium borohydride and propionic acid is about 1:3.8), add it in 12 hours, and then continue the reaction at 70°C After about 6 hours, cool down to room temperature, slowly pour the material into 100ml of ice water, add about 20g of hydrochloric acid with a mass concentration of 10% under stirring, and adjust the pH to about 2. The obtained product was distilled off under reduced pressure to remove the solvent tetrahydrofuran, and then extracte...

Embodiment 3

[0053] Embodiment 3: Preparation of compound 3 (melatonin)

[0054] (compound 3)

[0055] 3.5g of the compound As the starting reactant (the starting reactant can be prepared according to the preparation method described in the document Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol.251; (1960); p.394), 1.9 g of hydroboration Sodium was added in 40ml of anhydrous tetrahydrofuran, heated to reflux, wherein the molar ratio of the initial reactant to sodium borohydride was about 1:5, and a mixed solution of 20.9g of acetic acid and 20ml of anhydrous tetrahydrofuran (sodium borohydride and acetic acid) was slowly added dropwise. The molar ratio is about 1:3.5), and the addition was completed in 12 hours, and then the reaction was continued at 70°C for about 6 hours, and the temperature was lowered to room temperature, and the material was slowly poured into 100ml of ice water, and about 20g of hydrochloric acid with a mass concentration of 10% was add...

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Abstract

The invention discloses a preparation method of amide. The amide is the amide containing the structure shown in the specification. The method comprises the following step: carrying out one-step reaction by adopting a corresponding amide type compound as a starting reactant, a reducing agent and a corresponding acid to prepare a final amide product. According to the preparation method disclosed by the invention, the reaction steps are reduced, the cost can be effectively reduced, and the process flow is simplified.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for preparing an amide, the amide is a melatonin receptor agonist amide, and the method adopts the corresponding amide compound as an initial reactant, reducing Reagents and corresponding acids were used to prepare the final amide products in a one-step process. Background technique [0002] Melatonin (MT) is an indole compound and an amide hormone secreted by the pineal gland. [0003] [0004] Melatonin receptors are divided into three subtypes, namely MT 1 , MT 2 and MT 3 , studies have shown that only MT 1 and MT 2 Subtypes are associated with regulation of circadian rhythms. By activating these several melatonin receptor subtypes, it inhibits adenylyl cyclase and reduces cAMP release. Selective activation of MT1 receptors can promote the occurrence of sleep, while selective activation of MT2 receptors has an important relationship with regulating sleep ti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/06C07D307/79C07D307/77C07D209/14C07C233/18C07C231/14
Inventor 刘永志张宏川刘瑾
Owner JINAN ZHIHE MEDICAL TECH
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