Preparation method for 3-amino-2, 2-dimethylpropionamide

A technology of dimethylpropionamide and dimethylcyanoacetamide, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of increasing the cost and danger of production, and achieve the effects of simple operation, environmental protection and low preparation cost

Inactive Publication Date: 2013-10-02
SUZHOU FUSHILAI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic route can meet the requirements of industrial production, but since the steps of ammonolysis and cyano group reduction require heating and pressurized production equipment, it will undoubtedly increase the cost of production and the danger in the operation process

Method used

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  • Preparation method for 3-amino-2, 2-dimethylpropionamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A) Preparation of dimethylcyanoacetamide:

[0026] Add cyanoacetamide into the reaction vessel (with a stirring device) filled with organic solvent, that is, tetrahydrofuran, wherein: the weight ratio of tetrahydrofuran to cyanoacetamide is 30:1, and stir for 30 minutes at a temperature of -5°C , after stirring and dissolving, add sodium hydride with a mass percentage concentration of 60%, and stir the reaction for 120min under the condition of controlling the temperature at -5°C. After the stirring reaction is completed, slowly add dimethyl sulfate for alkylation reaction. The temperature of the alkylation reaction is 20°C, and the time of the alkylation reaction is 12h. After the alkylation reaction is completed, add saturated NH 4 Cl aqueous solution, distill off the tetrahydrofuran solvent, then extract with ethyl acetate, wash with water, and spin-dry (spin dry) to obtain the primary product of dimethyl cyanoacetamide in the form of light yellow solid powder, that ...

Embodiment 2

[0030] A) Preparation of dimethylcyanoacetamide:

[0031] Add cyanoacetamide in the reaction vessel (with stirring device) filled with organic solvent, that is, 2-methyltetrahydrofuran, wherein: the weight ratio of 2-methyltetrahydrofuran to cyanoacetamide is 50:1, in Stir at -5°C for 30 minutes, add sodium hydride with a mass percentage concentration of 60% after stirring and dissolving, and stir and react for 30 minutes at a controlled temperature of 10°C. After the stirring reaction is completed, slowly add diethyl sulfate dropwise Carry out the alkylation reaction, the temperature of the alkylation reaction is 0°C, and the time of the alkylation reaction is 24h. After the alkylation reaction is completed, add saturated NH 4 Cl aqueous solution, distill off the tetrahydrofuran solvent, then extract with ethyl acetate, wash with water, and spin-dry (spin dry) to obtain the primary product of dimethyl cyanoacetamide in the form of light yellow solid powder, that is, to obtain...

Embodiment 3

[0036] A) Preparation of dimethylcyanoacetamide:

[0037] Add cyanoacetamide in the reaction vessel (with stirring device) filled with organic solvent, that is, 2-methyltetrahydrofuran, wherein: the weight ratio of 2-methyltetrahydrofuran to cyanoacetamide is 10:1, in Stir at -5°C for 30 minutes, add sodium hydride with a mass percentage concentration of 60% after stirring and dissolving, and stir for 180 minutes at a controlled temperature of -10°C. After the stirring reaction is completed, slowly add methyl iodide dropwise to carry out Alkylation reaction, the temperature of the alkylation reaction is 10°C, the time of the alkylation reaction is 8h, and saturated NH 4 Cl aqueous solution, distill off the tetrahydrofuran solvent, then extract with ethyl acetate, wash with water, and spin-dry (spin dry) to obtain the primary product of dimethyl cyanoacetamide in the form of light yellow solid powder, that is, to obtain crude dimethyl cyanoacetamide Acetamide, then recrystalli...

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Abstract

The invention relates to a preparation method for 3-amino-2, 2-dimethylpropionamide, belonging to the technical field of drug intermediate preparation. The preparation method comprises the steps of adding cyanoacetamide in organic solvent, agitating and dissolving the cyanoacetamide, adding sodium hydride, dropping alkylating agent for alkylation reaction, adding saturated NH4Cl aqueous solution into the system, evaporating to remove the solvent, and performing ethyl acetate extraction, water washing and spin-drying to obtain crude dimethylcyanoacetamide, and performing recrystallization by using petroleum ether and ethyl acetate to obtain dimethylcyanoacetamide; weighing the dimethylcyanoacetamide and catalyst, adding and agitating the dimethylcyanoacetamide and the catalyst in mixed solution of organic solvent and water, adding reducing agent for reduction reaction, dropping acid solution till the pH (potential of Hydrogen) value of the reaction solution reaches a value of strong acidity, then dropping alkali solution till the pH value reaches a value of weak alkalinity, finally performing extraction by using extraction agent, drying by using drying agent, performing filtration and evaporating to remove the solvent to obtain finished products. The preparation method for the 3-amino-2, 2-dimethylpropionamide has the advantages that the cost is low; the environment is protected, the reaction steps are short and the method is simple to operate; and the yield and the product purity are high.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical intermediates, and in particular relates to a preparation method of 3-amino-2,2-dimethylpropionamide. Background technique [0002] Aliskiren is a new generation of non-peptide renin blocker. It is a new type of compound designed by the crystal structure analysis and computer model of the early renin blocker compound. It contains the previous renin blocker. The extended peptide-like structure is a potent, low molecular weight (relative molecular weight 610), non-peptide, highly selective renin blocker drug. Aliskiren first acts on the renin-angiotensin system, which is different from the existing drugs acting on angiotensin-converting enzyme inhibitors and angiotensin II receptor antagonists, and provides the ability to block the renin-angiotensin system. A whole new way. In March 2007, it was first approved for marketing in the United States, used alone or in combination f...

Claims

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Application Information

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IPC IPC(8): C07C237/06C07C231/12
Inventor 钱庆付任重丁建飞
Owner SUZHOU FUSHILAI PHARMA CO LTD
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