The preparation method of 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline

A technology of tert-butoxycarbonylpiperazine and aniline, which is applied in the field of preparation of 4-aniline, can solve the problems of low yield of target products, environmental and health hazards, and long synthesis routes, and avoid the use of heavy metals and hydrogen environments, Reduced production of by-products and low cost effects

Active Publication Date: 2020-07-31
深圳蓝新科技有限公司
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  • Abstract
  • Description
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Problems solved by technology

[0005] The purpose of the present invention is to overcome the above-mentioned deficiency of prior art, provide a kind of preparation method of 4-(1-tert-butoxycarbonylpiperazin-4-yl) aniline, to solve existing photocatalytic synthesis 4-(1-tert Butoxycarbonylpiperazin-4-yl) aniline has a long synthetic route, and the target product yield is low, and there are certain harmful technical problems to the environment and health

Method used

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  • The preparation method of 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline
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  • The preparation method of 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline

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preparation example Construction

[0010] The invention provides a preparation method of 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline. The preparation method of described 4-(1-tert-butoxycarbonylpiperazin-4-yl) aniline comprises the steps:

[0011] Add the aniline, piperazine-1-carboxylic acid tert-butyl ester, and acridinium salt photocatalyst into the solvent, and carry out light reaction under the condition of the presence of an oxidizing agent to generate 4-(1-tert-butoxycarbonylpiperazine-4 -yl) aniline.

[0012] Specifically, in the light reaction, the aniline and piperazine-1-carboxylic acid tert-butyl ester generate the product compound 4-( 1-tert-butoxycarbonylpiperazin-4-yl)aniline. The chemical reaction formula of the light reaction is as follows:

[0013]

[0014] Wherein, the acridinium salt promotes the condensation reaction of the aniline and tert-butyl piperazine-1-carboxylate under light conditions. In one embodiment, the acridinium salt photocatalyst includes at least one of the follo...

Embodiment 1

[0025] This example provides a preparation method of 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline. The synthetic method of described 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline:

[0026] Add aniline, piperazine-1-carboxylic acid tert-butyl ester, acridinium salt visible light catalyst, 2,2,6,6-tetramethylpiperidine-nitrogen-oxide into anhydrous dichloroethane, and then use oxygen The reaction environment was replaced three times, irradiated with a blue LED, and the reaction time was 10 h. After the reaction was completed, the filtrate was spin-dried and separated by column chromatography to obtain the target product as a colorless white solid with a yield of 95%.

[0027] Among them, aniline, piperazine-1-carboxylic acid tert-butyl ester, acridinium salt, 2,2,6,6-tetramethylpiperidine-nitrogen-oxide and anhydrous dichloroethane are added according to the following ratio: For every 2mL of anhydrous dichloroethane, add 0.2mmol, 1.0eq of aniline, 0.2mmol, 1.0eq of tert-but...

Embodiment 2

[0032] This example provides a preparation method of 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline. The synthetic method of described 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline:

[0033] Add aniline, piperazine-1-carboxylic acid tert-butyl ester, acridinium salt visible light catalyst, 2,2,4,6,6-pentamethylpiperidine-nitrogen-oxide into anhydrous dichloroethane, and then The reaction environment was replaced by oxygen three times, irradiated with a blue LED, and the reaction time was 10 h. After the reaction was completed, the filtrate was spin-dried and separated by column chromatography to obtain the target product as a colorless white solid with a yield of 93%.

[0034]Among them, aniline, piperazine-1-carboxylic acid tert-butyl ester, acridinium salt, 2,2,4,6,6-pentamethylpiperidine-nitrogen-oxide and anhydrous dichloroethane follow the following ratio Addition: Add 0.2mmol, 1.0eq of aniline, 0.2mmol, 1.0eq of tert-butyl piperazine-1-carboxylate, 0.01mmol, 0.1eq of ...

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Abstract

The invention discloses a preparation method of 4-(tert-butyl 1-piperazinecarboxylate-4-yl)aniline. The preparation method of the 4-(tert-butyl 1-piperazinecarboxylate-4-yl)aniline comprises the following steps that aniline, piperazine-1-tert-butyl formate and acridine salt photocatalysts are added into a solvent; illumination reaction is performed under the condition of oxidizing agent existence;the 4-(tert-butyl 1-piperazinecarboxylate-4-yl)aniline is generated. The preparation method of the 4-(tert-butyl 1-piperazinecarboxylate-4-yl)aniline has the advantages that the 4-(tert-butyl 1-piperazinecarboxylate-4-yl)aniline is synthesized in one step; on one hand, the synthesis path of the 4-(tert-butyl 1-piperazinecarboxylate-4-yl)aniline is effectively shortened; the generation of by-products is effectively reduced; the target product yield is improved; on the other hand, only photocatalysts and oxidizing agents are used, so that the preparation method is safe and achieves an environment-friendly effect; the cost is low.

Description

technical field [0001] The invention belongs to the technical field of organic medicinal chemistry, and in particular relates to a preparation method of 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline. Background technique [0002] 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline is an important chemical raw material. The traditional method of synthesizing 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline has the disadvantages of high pollution and low atomic economy. In order to overcome the shortcomings of the traditional synthesis method, a photocatalytic synthesis of 4 -(1-tert-butoxycarbonylpiperazin-4-yl)aniline, the specific chemical reaction formula is as follows: [0003] [0004] The current photocatalytic method for synthesizing 4-(1-tert-butoxycarbonylpiperazin-4-yl)aniline is through a two-step linear reaction, the first step is a metal-catalyzed coupling reaction, and the second step is palladium carbon Catalytic hydrogenation process. Heavy metals are used in ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/205
CPCC07D295/205
Inventor 黄湧韩珂珩周海鹏张强韩辉丁小妹王雷锋
Owner 深圳蓝新科技有限公司
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