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A kind of technique for preparing 3-phenyl-4-aminobutyric acid hydrochloride

A technology of aminobutyric acid hydrochloride and methyl nitrobutyrate, which is applied in the field of chemistry, can solve the problems of low overall yield of target products, many reaction steps, and difficult operation, and achieve improved hydrogenation efficiency and good reaction rate Easy and convenient effect with yield and control

Active Publication Date: 2017-02-15
TIANJIN JUDE TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has many reaction steps, long route and low overall yield of target product
The hydrogenation reaction in the route needs to be carried out at forty atmospheres, which is difficult to operate

Method used

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  • A kind of technique for preparing 3-phenyl-4-aminobutyric acid hydrochloride
  • A kind of technique for preparing 3-phenyl-4-aminobutyric acid hydrochloride
  • A kind of technique for preparing 3-phenyl-4-aminobutyric acid hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Take 9.8g of methyl cinnamate and 40ml of nitromethane in a 100ml three-neck flask, stir, heat up to 50°C, then add 1.5g of triethylamine and 0.5g of anhydrous MgCl2, maintain 50°C for 10h, TLC The detection response is complete.

[0037] Distill under reduced pressure to remove excess nitromethane, then transfer the solution with a small amount of ethyl acetate, wash with 5% hydrochloric acid for 3 times, then wash with water until neutral, and then wash with anhydrous MgSO 4Dry to obtain 12.98 g of 3-phenyl-4-nitrobutyric acid methyl ester, the yield is 94.1%

[0038] Take 12.98g of methyl 3-phenyl-4-nitrobutyrate, add 200ml of ethanol, then add 0.13g of Raney nickel into the reaction system, stir, heat up to 50°C, and feed hydrogen gas (bubble), to The reaction was monitored by TLC, and the reaction time was about 8 h. After filtration, the resulting filtrate was distilled under reduced pressure to obtain 8.33 g of 3-phenylvalerolactam, with a yield of 95.7%.

[0...

Embodiment 2

[0042] Take 49g of methyl cinnamate and 200ml of nitromethane in a 500ml three-neck flask, stir, heat up to 50°C, then add 7.5g of triethylamine and 2.5g of anhydrous MgCl2, maintain 50°C for 10h, and detect by TLC The response is complete.

[0043] Distill under reduced pressure to remove excess nitromethane, then transfer the solution with a small amount of ethyl acetate, wash with 5% hydrochloric acid for 3 times, then wash with water until neutral, and then wash with anhydrous MgSO 4 Dry to obtain 64.9 g of methyl 3-phenyl-4 nitrobutyrate, the yield is 94.1%

[0044] Take 64.9g of 3-phenyl-4-nitrobutyric acid methyl ester, add 1000ml of ethanol, then add 0.65g of Raney nickel into the reaction system, stir, heat up to 50°C, and feed hydrogen gas (just bubbling), to The reaction was monitored by TLC, and the reaction time was about 12 h. After filtration, the resulting filtrate was distilled under reduced pressure to obtain 41.6 g of 3-phenylvalerolactam, with a yield of ...

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PUM

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Abstract

The invention provides a technology for preparing 3-phenyl-4-aminobutyric acid hydrochloride. According to the technology, methyl cinanmate and nitromethane are used as oligomers, nitromethane is taken as an oligomer and a solvent, and a series of troubles in treatment caused when a third reagent is introduced as a solvent is avoided; 94.1% 3-phenyl-4-nitryl methyl butyrate can be obtained by a triethylamine and anhydrous MgC12 mixed catalyst, and the reaction efficiency is improved; raney nickel is used as a catalyst for converting the 3-phenyl-4-nitryl methyl butyrate into 3-phenyl valerolactam, the hydrogenation efficiency is improved, and the conversion rate of the 3-phenyl-4-nitryl methyl butyrate reaches 95.7%; and a methanol and dichloromethane mixed solvent serves as a solvent used for recrystallizing 3-phenyl-4-aminobutyric acid hydrochloride; and through recrystallization, the purity of the target product is above 99.0%. The technology has the advantages that reaction conditions are mild and easy to control, hydrogenation is finished in one step, high pressure does not need to be maintained; as long as bubbling is carried out and hydrogen atmosphere is maintained, the good reaction rate and yield can be obtained; and the control is simple and convenient.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a process for preparing 3-phenyl-4-aminobutyric acid hydrochloride. Background technique [0002] γ-Aminobutyric acid (GABA) is a non-protein amino acid widely distributed in animals and plants. It is an inhibitory neurotransmitter that exists in the brain and spinal cord of mammals, and participates in the physiological activities of brain circulation in humans or animals. In addition to the brain and spinal cord, GABA has been found in nearly 30 peripheral tissues of various mammals. Studies have shown that γ-aminobutyric acid is a physiologically active ingredient that can lower blood pressure, resist convulsions, increase neurotrophy, improve brain function, promote long-term memory, promote growth hormone secretion, and activate kidney and liver functions. [0003] GABA ingested from the outside cannot pass through the blood-brain barrier due to its poor lipophilicity, so it canno...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/34C07C227/22C07C227/42
Inventor 多文彬
Owner TIANJIN JUDE TECH
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