Preparation method of 4-aminobutanol

A technology of aminobutanol and chlorobutanol, which is applied to the preparation of aminohydroxyl compounds, the preparation of organic compounds, chemical instruments and methods, etc., which can solve the problems of unsuitable large-scale industrial production, harsh preparation conditions, and natural safety hazards of catalysts, etc. problems, to achieve the effects of large-scale industrial production, simple and easy post-processing, and significant social and economic benefits

Active Publication Date: 2018-10-16
HENAN CHEM IND RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For the research of 4-aminobutanol, the experts initially prepared 4-aminobutanol by one-step reaction of azide compound. This method can be completed in one step, but there are certain hidden dangers of explosion and the yield is low; -Halogenated butyronitrile is used as a raw material, the nitrile group is reduced to obtain an amino group, and the product is hydrolyzed under high temperature and strong alkali conditions, the reaction conditions are very harsh and the yield is low; in the 1990s, Stein et al. 4-aminobutanol is prepared by reductive amination of ene-1,4-diol. This method not only needs harsh conditions of high pressure, but also needs expensive rhodium acetate catalyst in the reaction process, that is, the preparation conditions are harsh, the cost is high, and the yield is high. Low; subsequently, Ma Nan et al. used 4-aminobutyric acid as a raw material to prepare 4-aminobutanol through Boc-protected

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  • Preparation method of 4-aminobutanol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Add 74.08g phthalimide potassium salt, 500ml dimethylformamide, 0.7g tetrabutylammonium bromide in a three-necked flask with a volume of 1L, mix and stir to obtain the mixture, and then pour it under room temperature 52.13 g of 4-chlorobutanol was added dropwise into the mixture (stirring while adding, the dropwise addition was completed in 0.5 h), and after the dropwise addition was completed, the reaction was completed by stirring at 80°C for 9 h to obtain a mixed solution of the intermediate;

[0030] Then, under the action of the water pump, the mixed solution of the intermediate was subjected to rotary evaporation, and the dimethylformamide was removed by evaporation. After the evaporation was completed, 300ml of dichloromethane was added to the remaining product and mixed and stirred evenly to obtain the intermediate. Dichloromethane solution; Then first use the sodium hydroxide solution that mass concentration is 2% to the dichloromethane solution washing extr...

Embodiment 2

[0038] (1) Add 74.08g phthalimide potassium salt, 500ml dimethyl sulfoxide, 0.7g hexadecyldimethylammonium bromide in a three-necked flask with a volume of 1L, mix and stir to obtain a mixture, Then, 52.13g of 4-chlorobutanol was added dropwise to the mixture at room temperature (stirring while adding, and the dropwise addition was completed in 0.5h). mixture;

[0039] Then under the effect of water pump, the mixed solution of the intermediate is subjected to rotary evaporation, and the dimethyl sulfoxide is removed by evaporation. After the evaporation is completed, 300ml of dichloromethane is added to the remaining product and mixed and stirred to obtain the intermediate. Dichloromethane solution; Then first use the sodium hydroxide solution that mass concentration is 2% to the dichloromethane solution washing extraction of intermediate twice (each with 100ml), then wash and extract once with 100ml saturated sodium chloride solution, Wash the organic phase obtained after th...

Embodiment 3

[0047] (1) Add 74.08g phthalimide potassium salt, 500ml dimethyl sulfoxide, 0.7g hexadecyldimethylammonium bromide in a three-necked flask with a volume of 1L, mix and stir to obtain a mixture, Then, 56.47g of 4-chlorobutanol was added dropwise to the mixture at room temperature (stirring while adding, and the dropwise addition was completed in 0.5h). mixture;

[0048] Then under the effect of water pump, the mixed solution of the intermediate is subjected to rotary evaporation, and the dimethyl sulfoxide is removed by evaporation. After the evaporation is completed, 300ml of dichloromethane is added to the remaining product and mixed and stirred to obtain the intermediate. Dichloromethane solution; Then first use the sodium hydroxide solution that mass concentration is 2% to the dichloromethane solution washing extraction of intermediate twice (each with 100ml), then wash and extract once with 100ml saturated sodium chloride solution, Wash the organic phase obtained after th...

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Abstract

The invention provides a preparation method of 4-aminobutanol. The method comprises the steps of taking potassium phthalimide and 4-chlorbutanol as raw materials, and preparing an intermediate in thepresence of a solvent and a phase transfer catalyst; and then hydrolyzing the intermediate under the effect of an alkaline solution to obtain the 4-aminobutanol. The raw materials used in the method are simple, the cost is low, the reaction conditions are gentle, potential safety hazards do not exist, and additional reactions hardly exist in a reaction process of the various used raw materials; and in a preparation process, substances which are difficult to separate are not generated, and aftertreatment is simple and is easy to operate; and therefore, the yield of the 4-aminobutanol is greatlyimproved, the utilization rate of the raw materials is increased, and the production cost is reduced. Under the condition of low cost, the yield of products is increased obviously, and the economic benefit is remarkable.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 4-aminobutanol. technical background [0002] 4-Aminobutanol, the English name is 4-aminobutan-1-butanol, and its molecular weight is 89.14. It is an important pharmaceutical and chemical intermediate. Because it has active groups such as amino and hydroxyl groups at both ends of its molecule, it can further produce chemical reaction, introducing nitrogen atoms or other groups, so many domestic and foreign experts and scholars have done a lot of research on the preparation process of 4-aminobutanol. For the research of 4-aminobutanol, the experts initially prepared 4-aminobutanol by one-step reaction of azide compound. This method can be completed in one step, but there are certain hidden dangers of explosion and the yield is low; -Halogenated butyronitrile is used as a raw material, the nitrile group is reduced to obtain an amino gr...

Claims

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Application Information

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IPC IPC(8): C07C213/02C07C215/08
CPCC07C213/02C07D209/48C07C215/08
Inventor 刘菲赵胜勇黄蓓张谦华范金周赵怡丽王芳王延花霍二福袁竹青陈秋丽王静刘玉霞
Owner HENAN CHEM IND RES INST
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