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Novel synthesis process for oxiracetam key intermediate 2-(2,4-dioxopyrrolidine-1-yl)-acetamide

A technology of dioxopyrrolidine and intermediates, which is applied to the new synthesis process field of oxiracetam key intermediate 2-(2,4-dioxopyrrolidin-1-yl)-acetamide, can solve the problem of Lack of efficient synthesis methods for intermediates, low yields, long synthesis steps, etc., to achieve the effects of good industrial application prospects, high yields, and short steps

Active Publication Date: 2015-01-14
ZHEJIANG UNIV OF TECH
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Problems solved by technology

[0011] Because the reaction selectivity of each step in this synthetic route is high, and related intermediates can be effectively purified, it is easier to obtain high-purity oxiracetam products, but its intermediate 2-(2,4-dioxopyrrole Alkyl-1-yl)acetamides (see 2 for structure) have long synthetic steps,
[0012] The yield is low, only 35%. At present, there is a lack of an efficient synthetic method for this intermediate, so it is necessary to explore its synthetic method to obtain a method suitable for industrial production and efficient synthesis of this intermediate

Method used

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  • Novel synthesis process for oxiracetam key intermediate 2-(2,4-dioxopyrrolidine-1-yl)-acetamide
  • Novel synthesis process for oxiracetam key intermediate 2-(2,4-dioxopyrrolidine-1-yl)-acetamide
  • Novel synthesis process for oxiracetam key intermediate 2-(2,4-dioxopyrrolidine-1-yl)-acetamide

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Embodiment

[0023] In a three-necked flask, add 8.0 g (0.075 mol) glycinamide hydrochloride, 20.2 g (0.029 mol) potassium carbonate, and 100 ml absolute ethanol. Stir at 45°C for 30 minutes, and slowly add 10 g (0.06 mol) dropwise. ) Ethyl 4-chloroacetoacetate, drip and reflux for 5h. , Filtered while hot, removed part of the ethanol under reduced pressure, and the residue was cooled and filtered to obtain 6.7 g of the key intermediate of 2-(2,4-dicarbonylpyrrolidone-1-yl)-acetamide with a yield of 72.0%. 1 H NMR (500 MHz, DMSO- d 6 ) δ 7.67 (s, 1H), 7.49 (s, 1H), 7.22 (s, 1H), 4.65 (s, 2H), 4.48 (s, 1H), 3.67 (d, J = 5.6 Hz, 2H); 13 C NMR (125 MHz, DMSO- d 6 ) δ 174.71 (s), 169.90 (s), 168.97 (s), 79.37 (s), 67.16 (s), 46.90 (s); GC / MS: m / z=156 [M] + .

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Abstract

The invention provides a novel synthesis process for preparing an oxiracetam key intermediate 2-(2,4-dioxopyrrolidine-1-yl)-acetamide by using 4-halogenated acetoacetic ester and glycinamide hydrochloride as raw materials by virtue of a 'one-pot method'. The novel synthesis process has the advantages of being few in reaction steps, high in yield, cheap and easily available in raw materials, simple in post-treatment, has few waste gas, waste water and waste residues and the like.

Description

technical field [0001] The invention relates to a new preparation method for preparing 2-(2,4-dioxopyrrolidin-1-yl)-acetamide, a key intermediate of oxiracetam. Background technique [0002] Oxiracetam, chemical name: 4-hydroxypyrrolidone-2-acetamide, molecular formula: C 6 h 10 N 2 o 3 , the structure is shown in 1: [0003] [0004] 1 [0005] Oxiracetam is a synthetic cyclic derivative of hydroxyaminobutyric acid (GABOB), also known as Olamide, Oxypyramide, and its trade names are neuromet, Heupan, Jianlangxing, etc. It was synthesized for the first time in 1974 by the company and listed in Italy in 1987. It is one of the drugs approved by the US FDA for the treatment of senile dementia. The synthesis routes reported so far generally have shortcomings such as difficult purification or long synthesis routes. As proposed in Japanese Patent JP62026267, a kind of 3-hydroxy-4-halobutanoic acid ethyl ester and glycinamide is used as raw materials to directly prepare ox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/36
CPCC07D207/36
Inventor 叶青高建荣任锋李郁锦韩亮顾凯钟健
Owner ZHEJIANG UNIV OF TECH
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