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Preparation method of 1-[2-(2-hydroxyethoxy) ethyl] piperazine

A technology of hydroxyethoxy and piperazine, which is applied in the field of organic chemical material synthesis, can solve the problems of increased post-processing difficulty, difficulty in industrial production, and high reaction temperature, and achieves good promotion and application value, simple operation, and high reaction conversion rate Effect

Pending Publication Date: 2021-02-05
GAOYOU CITY ORGANIC CHEM FACOTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The total reaction yield of this method is 87.4%, but the reaction temperature is too high, and the use of DMF as the reaction solvent will increase the difficulty of post-processing, which is not easy for industrial production

Method used

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  • Preparation method of 1-[2-(2-hydroxyethoxy) ethyl] piperazine
  • Preparation method of 1-[2-(2-hydroxyethoxy) ethyl] piperazine
  • Preparation method of 1-[2-(2-hydroxyethoxy) ethyl] piperazine

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Experimental program
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Effect test

Embodiment 1

[0032] The preparation of 1-[2-(2-hydroxyethoxy) ethyl] piperazine adopts the following process route:

[0033]

[0034] In a 250ml round bottom flask, add 1,1'-methylenethiobispiperazine (2.14g, 10mmol), 60ml methanol, chlorodiethylene glycol (2.739g, 22mmol), sodium carbonate (1.260g, 12mmol) ), heated to reflux for 8h (TLC plate tracking reaction progress); after the reaction, cool down to 30°C, add K 2 S 2 o 8 (5.40g, 20mmol), then heated up at 60°C and reacted for 6h (TLC plate followed the reaction process); after the reaction, methanol was evaporated to dryness, and purified water (50ml) was added and extracted with dichloromethane (20ml*3), and the layers were separated. The organic phase was dried over anhydrous sodium sulfate and concentrated to obtain a crude product, which was purified by column chromatography to obtain 1.401 g of a pure product with a yield of 80.5%.

[0035] Adopt nuclear magnetic resonance instrument (AVANCE DMX Ⅱ Ⅰ 400M, Bruker company) t...

Embodiment 2

[0041] Screening of the Feed Ratio of 1,1'-Methylenethiobispiperazine and Chlorodiethylene Glycol

[0042] Experimental conditions of the present embodiment, charging amount are identical with embodiment 1, select different feeding ratios (raw material II: raw material III) to carry out experiment, specifically as shown in table 1:

[0043] Table 1

[0044]

[0045] It can be seen from Table 1 that when the feeding ratio of 1,1'-methylenethiobispiperazine and chlorodiethylene glycol is 1:2, the reaction yield is 71%, when 1,1'-methylenethio When the feeding ratio of bispiperazine and chlorodiethylene glycol is 1:2.2, the reaction yield is 80.5%. However, if the feeding amount of chlorodiethylene glycol continues to increase, the reaction yield does not increase significantly. In summary, the present invention selects 1,1'-methylenethiobispiperazine and chlorodiethylene glycol at a feed ratio of 1:(2-3), most preferably 1:2.2 for the reaction.

Embodiment 3

[0047] Screening of oxidants

[0048]Experimental conditions of the present embodiment, charging amount are identical with embodiment 1, select different oxidant (2 times (mol ratio) of raw material II) to carry out experiment, specifically as shown in table 2:

[0049] Table 2

[0050] oxidizing agent yield 1 tert-butanol peroxide 51％ 2 Triethylenediamine 46％ 3 potassium persulfate 80.5％ 4 sodium persulfate 76.5％

[0051] As can be seen from Table 2, when selecting triethylenediamine as the oxidant, the reaction yield is the lowest, only 46%. When sodium persulfate is used as the oxidant, the reaction yield is 76.5%. The rate is the highest, being 80.5%; In summary, the preferred potassium persulfate of the present invention is used as the reaction oxidant.

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Abstract

The invention discloses a preparation method of 1-[2-(2-hydroxyethoxy) ethyl] piperazine in the technical field of organic chemical material synthesis, which comprises the following steps of: carryingout condensation reaction in a solvent to prepare an intermediate by using 1, 1'-methylene thio dipiperazine and chlorodiethylene glycol as starting materials and sodium carbonate as an acid-bindingagent; and adding an oxidant, and carrying out cracking reaction to obtain 1-[2-(2-hydroxyethoxy) ethyl] piperazine. The method has the advantages of short reaction steps, mild reaction conditions andhigh product yield, and a new method is provided for preparing 1-[2-(2-hydroxyethoxy) ethyl] piperazine. The target product provided by the invention has huge application value in the aspects of chemical pharmacy, organic synthesis and the like.

Description

technical field [0001] The invention belongs to the technical field of synthesis of organic chemical materials, and in particular relates to a synthesis method of 1-[2-(2-hydroxyethoxy)ethyl]piperazine. Background technique [0002] 1-[2-(2-hydroxyethoxy) ethyl] piperazine (HEEP) is a kind of important organic synthesis intermediate, and its structure is as shown in I below: [0003] [0004] Widely used in chemical pharmaceuticals, polymer materials, dyes and fine chemicals and other industries. In chemical pharmaceuticals, 1-[2-(2-hydroxyethoxy)ethyl]piperazine is used in the synthesis of antiallergic drug cetirizine hydrochloride, antipsychotic drug quetiapine fumarate and anxiolytics An important intermediate of Antalol; in terms of polymer materials, 1-[2-(2-hydroxyethoxy) ethyl]piperazine can be used to modify polymer materials, and bonded to self-assembled monomers of polyamines A modified polymer film with anti-microbial adsorption capacity is formed on the poly...

Claims

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Application Information

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IPC IPC(8): C07D295/088
CPCC07D295/088
Inventor 瞿军吴宏祥掌鹏程沈润溥
Owner GAOYOU CITY ORGANIC CHEM FACOTRY
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