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Method for normal-temperature catalytic synthesis of 1,4-dihydropyridine compounds

A technology for dihydropyridine and compounds, which is applied in the field of catalytic synthesis at room temperature, can solve the problems of large consumption of organic solvents, many post-processing steps, and large environmental pollution, and achieves the effects of convenient post-processing, convenient preparation, and wide source of raw materials

Inactive Publication Date: 2012-05-02
YANCHENG TEACHERS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This kind of extraction-drying-filtration-concentration-recrystallization has many post-processing steps, complicated process, large consumption of organic solvent, and large environmental pollution.

Method used

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  • Method for normal-temperature catalytic synthesis of 1,4-dihydropyridine compounds
  • Method for normal-temperature catalytic synthesis of 1,4-dihydropyridine compounds
  • Method for normal-temperature catalytic synthesis of 1,4-dihydropyridine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a 50mL round bottom flask, add 5mmol (0.53g) benzaldehyde, 10mmol (1.30g) ethyl acetoacetate, 5mmol (0.48g) ammonium carbonate, 1.0g catalyst, 20mL solvent, and stir in an open system at normal temperature and pressure 48 hours. After the reaction is completed, the filter residue is used as a catalyst, and the solvent separated from the filtrate by distillation can be recovered and recycled. The remaining crude product is recrystallized with absolute ethanol to obtain 4-phenyl-1,4-dihydropyridine product with a yield of 71%.

Embodiment 2

[0021] In a 50mL round bottom flask, add 5mmol (0.53g) benzaldehyde, 10mmol (1.30g) ethyl acetoacetate, 5mmol (0.48g) ammonium carbonate, 2.0g catalyst, 20mL solvent, and stir in an open system at normal temperature and pressure 24 hours. After the reaction is completed, the filter residue is used as a catalyst, and the solvent separated from the filtrate by distillation can be recovered and recycled. The remaining crude product is recrystallized with 95% ethanol to obtain 4-phenyl-1,4-dihydropyridine product with a yield of 65%.

Embodiment 3

[0023] In a 50 mL round bottom flask, add 5 mmol (0.53 g) of benzaldehyde, 10 mmol (1.30 g) of ethyl acetoacetate, 5 mmol (0.48 g) of ammonium carbonate, 1.5 g of catalyst, and 20 mL of solvent, and stopper the mouth of the flask to seal the reaction system. Stir at normal temperature and pressure for 30 hours. After the reaction is completed, the filter residue is used as a catalyst, and the solvent separated from the filtrate by distillation can be recovered and recycled. The remaining crude product is recrystallized with 95% ethanol to obtain 4-phenyl-1,4-dihydropyridine product with a yield of 67%.

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Abstract

The invention discloses a method for normal-temperature catalytic synthesis of 1,4-dihydropyridine compounds, which takes bread active dried yeast as a catalyst, aromatic aldehyde, ethyl acetoacetate and ammonium carbonate as raw materials and 2-methyltetrahydrofuran as a solvent and performs reaction in an open or closed system at normal temperature and under normal pressure with stirring. In the invention, filtration is carried out after reaction, filtrate is used as a catalyst, and the solvent in the filtrate can be recovered and used by distillation. Compared with the prior art, the method has the advantages that: (1) the raw material resource is wide, the preparation is convenient, the byproduct which is carbon dioxide is convenient to treat afterwards, and organic ammonium salts including ammonium formate, ammonium acetate and the like are difficult to be treated afterwards; (2) the raw material of the catalyst is widely available and safe and nontoxic; (3) the raw material for preparing the solvent is furfuraldehyde prepared by processing by products such as corncobs and bagasse, is a pure green product and is environment-friendly; and (4) the reaction conditions are mild, and a condenser tube blockage problem caused by decomposition and condensation under a heating condition is solved.

Description

a technical field [0001] The invention relates to a novel method for catalytically synthesizing 1,4-dihydropyridine compounds at normal temperature, belonging to the technical field of biochemical industry. This method is suitable for the synthesis of 1,4-dihydrofuran in an open or closed system under normal temperature and pressure using an active dry yeast-flavored catalyst for bread, aromatic aldehydes, acetoacetate, and ammonium carbonate as raw materials, and 2-methyltetrahydrofuran as a solvent. In the case of hydropyridine compounds. Two background technology [0002] 1,4-Dihydropyridine compounds are widely used in biology and medicine. Its representative compound, nifedipine, is the first-generation calcium antagonist, especially suitable for the treatment of angina pectoris, arrhythmia, hypertension and other diseases caused by coronary artery spasm. It also has new uses for treating gastrointestinal diseases, Raynaud's disease, primary pulmonary hypertension and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/12
CPCY02P20/584
Inventor 方东
Owner YANCHENG TEACHERS UNIV