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Preparation method for 4-amino-3-phenylbutyric acid

A technology of phenylbutyric acid and phenylvaleric acid, which is applied in the preparation of organic compounds, chemical instruments and methods, and cyanide reaction preparation, etc., can solve problems such as unsafe hidden dangers, risks in factory production, and complicated operations. , to achieve the effect of simple operation, mild reaction conditions and high yield

Inactive Publication Date: 2011-07-06
上海新浦特种助剂有限公司
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Problems solved by technology

The process uses toxic, flammable and explosive nitromethane, which poses unsafe hidden dangers in factory production; and the hydrogenation reduction step involves high-pressure hydrogenation, complicated operation, and large-scale production in the factory is also risky

Method used

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  • Preparation method for 4-amino-3-phenylbutyric acid
  • Preparation method for 4-amino-3-phenylbutyric acid

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Embodiment Construction

[0027] The preferred implementation of the present invention will be described in detail below according to the examples.

[0028] 1, 2, the synthesis of 4-diacetyl-3-phenyl-pentanedionate diethyl ester (1)

[0029] Add 26.5 g of benzaldehyde, 65 g of ethyl acetoacetate, and 106 g of 95% ethanol into the reaction flask, add 4 g of piperidine under stirring, react for 5.5 hours, stop stirring, and stand still. From the beginning of adding piperidine to the end of the reaction, a total of 36 hours, the temperature was controlled at less than 40°C. Cool to room temperature, suction filter after 2 hours, wash the filter cake with a small amount of ethanol, recover the mother liquor and use it mechanically. The filter cake was dried to obtain 68 g of the needle-like crystal product 2,4-diacetyl-3-phenyl-pentanedionate (1), with a yield of 78.2%, Mp: 149-153° C., document (jour. Indianchem.soc., Vol.40, No.10, 1983) melting point: 150°C.

[0030] 2. Synthesis of 3-phenylglutaric ...

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Abstract

The invention provides a preparation method for 4-amino-3-phenylbutyric acid. The method comprises the following steps: step 1, benzaldehyde reacts with ethyl acetoacetate in a protonic solvent under the action of a condensation catalyst to generate 2,4-diacetyl-3- phenyl-pentanedionato diethyl ester (1); step 2, strongly alkaline solution is added in the 2,4-diacetyl-3-phenyl-pentanedionato diethyl ester (1) to obtain 3-phenylglutaric acid (2) after heating and decarbonylation; step 3, the 3-phenylglutaric acid (2) is subjected to ring-closing dehydration in a non-protonic solvent under the action of a dehydration catalyst to obtain 3-phenylglutaric anhydride step 4, the 3-(phenyl-glutaric anhydride) (3) is hydrolyzed with strong aqua ammonia to obtain 5-amino-5-oxo-3-phenyl-pentanoic acid (4); and step 5, the 5-amino-5-oxo-3-phenyl-pentanoic acid (4) and an oxidant are subjected to oxidation reaction under the alkaline condition to obtain 4-amino-3- phenyl butyric acid (5). The method has the advantages of easily-obtained inexpensive raw materials, normal reaction, simplicity and convenience in operation, moderate reaction conditions, security and high yield, and is suitable for industrial volume production.

Description

technical field [0001] The invention relates to a preparation method of 4-amino-3-phenylbutyric acid, which is suitable for industrial mass production. Background technique [0002] 4-amino-3-phenylbutyric acid (4-Amino-3-phenylbutyric acid), its structural formula (5) is: [0003] [0004] Very effective as an antidepressant. Therefore, it is very necessary to develop a process route that is suitable for industrial mass production, with readily available raw materials, mild reaction conditions, simple and safe operation, and high yield. [0005] At present, Chinese patent CN101033195A discloses the production process of 4-amino-3-phenylbutyrate hydrochloride: adopt benzoic acid and nitromethane to react to obtain nitrostyrene; this nitrostyrene and diethyl malonate Reaction to generate α-carbomethoxy-β-phenyl-γ-nitrobutyric acid methyl ester; then add nickel, feed hydrogen, and reduce reaction under 4MPa pressure to obtain α-carbocarboxy-β-phenyl-γ -Tetrahydropyrrolid...

Claims

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Application Information

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IPC IPC(8): C07C229/34C07C227/04
Inventor 苏莹周利张秋华
Owner 上海新浦特种助剂有限公司
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