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A kind of preparation method of Aniracetam

An Aniracetam and synthetic route technology, applied in the field of Aniracetam preparation, can solve the problems of difficult separation and purification of products, harsh reaction conditions, long synthesis routes, etc., and achieves cheap and easy-to-obtain raw materials, short reaction steps, and easy operation. simple effect

Active Publication Date: 2020-12-22
LONGXINING SHANGHAI PHARMA TECH CO LTD +1
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  • Description
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Problems solved by technology

[0014] It can be seen that the preparation method of Aniracetam provided in the prior art often has the following technical defects: the reaction conditions are harsh, the synthetic route is too long, the product yield is low, and the product separation and purification are difficult

Method used

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  • A kind of preparation method of Aniracetam
  • A kind of preparation method of Aniracetam
  • A kind of preparation method of Aniracetam

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preparation example Construction

[0034] According to the preferred embodiment provided by the present invention, the preparation method of Aniracetam comprises the following specific steps:

[0035] S1: Add the organic solvent, p-methoxybenzoic acid, and organic base into the flask together, then slowly add pivaloyl chloride dropwise under the cooling condition of an ice-water bath, after the drop is completed, stir the reaction for 0.5 to 8 hours,

[0036] S2: Add 2-pyrrolidone into the flask, heat to reflux, continue to stir and react for 6 to 24 hours, the reaction is complete, wash with water, wash with alkali, dry, concentrate, dissolve with ethanol, decolorize with activated carbon, filter while hot, cool and crystallize, Filter again, take the filter cake, and dry under reduced pressure to obtain the target product Aniracetam.

[0037] In a preferred embodiment, the organic base is selected from any one or more of the following: triethylamine, diisopropylethylamine, pyridine, N-methylmorpholine, tetram...

Embodiment 1

[0043] Add dichloromethane (250ml) in the flask, p-methoxybenzoic acid (30.4g), triethylamine (60.7g), slowly add pivaloyl chloride (25.3g) dropwise under ice-water bath cooling condition, dropwise finishes, Heat to reflux, stir for 2 hours; then, add 2-pyrrolidone (25.5 g), heat to reflux, continue to stir and react for 6 to 24 hours, until the reaction is complete, wash with water, wash with sodium carbonate aqueous solution, dry, concentrate, dissolve with ethanol, Activated carbon was decolorized, filtered while it was hot, cooled and crystallized, filtered again, the filter cake was taken, and dried under reduced pressure to obtain the target product Aniracetam (30.7g), with a yield of 70.2%.

[0044] Wherein, Aniracetam is characterized as follows:

[0045] 1 H NMR (400MHz, DMSO, TMS): δ7.57 (2H, d, J = 8.8Hz), 6.94 (2H, d, J = 8.8Hz), 3.81 (3H, s), 3.79~3.75 (2H, m ), 2.54~2.43(2H,m), 2.04~1.99(2H,m).

Embodiment 2

[0047] Add dichloromethane (250ml) in the flask, p-methoxybenzoic acid (30.4g), diisopropylethylamine (77.4g), slowly add pivaloyl chloride (25.3g) dropwise under ice-water bath cooling condition, After dripping, heat to reflux, stir and react for 2 hours; then, add 2-pyrrolidone (25.5 g), heat to reflux, continue to stir and react for 6 to 24 hours, until the reaction is complete, wash with water, wash with sodium hydroxide aqueous solution, dry, and concentrate, Dissolve with ethanol, decolorize with active carbon, filter while hot, cool and crystallize, filter again, take filter cake, dry under reduced pressure, obtain target product Aniracetam (31.2g), yield 71.2%.

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Abstract

The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of aniracetam. According to the preparation method of the aniracetam provided by the invention, a mixed acid anhydride intermediate is firstly generated by p-methoxybenzoic acid and pivaloyl chloride, and then the mixed acid anhydride intermediate reacts with 2-pyrrolidone to form a targetproduct, namely aniracetam. Therefore, the preparation method of the aniracetam has the advantages that the reaction steps are short, the reaction yield and the product purity are relatively high, rawmaterials are low in cost and easy to obtain, the operation is simple, and the method is suitable for large-scale industrial production and the like.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a preparation method of Aniracetam. Background technique [0002] Aniracetam (aniracetam, Aniracetam), the chemical name is 1-(4-methoxybenzoyl)-2-pyrrolidone, and its structural formula is as follows: [0003] [0004] As we all know, Aniracetam is a γ-lactam drug for improving brain function, which is mainly used clinically to treat sequelae of cerebrovascular diseases. In addition, Aniracetam can be used as an effective drug for the treatment of Alzheimer's disease. The drug can increase the level of acetylcholine in the brain of patients, which is beneficial to the transmission of cholinergic nerves. It has the characteristics of quick effect and low toxicity (Northwest Pharmaceutical Journal, 2014, 29(1), 67-69). [0005] The synthesis process of Aniracetam is provided in the prior art, for example, US Pat. No. 4,369,139 reports various synthesis routes. [0006] For...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/263
CPCC07D207/263
Inventor 朱宁李春成杨勤刚
Owner LONGXINING SHANGHAI PHARMA TECH CO LTD
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