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Preparation method of 1,11-di(1-bispiperdine)-3,9-dioxo-6-thia-hendecane

A dioxo, dipiperidine technology, applied in the field of fine chemicals, can solve the problems of easily polluted environment, low yield, strong volatility, etc., and achieves the effects of simple post-processing process, simple process steps, and avoiding environmental pollution.

Active Publication Date: 2013-09-11
沈阳感光化工研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1. There are many reaction steps and the post-treatment process is cumbersome
[0007] 2. Low yield and high cost
[0008] 3. N-chloroethylpiperidine hydrochloride is unstable after desalination, and the storage time is short. It must immediately enter the next step reaction, which is not convenient for industrial production
[0009] 4. A large amount of dichloromethane needs to be used in post-processing, which is highly toxic and volatile, easily pollutes the environment and endangers the health of operators

Method used

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  • Preparation method of 1,11-di(1-bispiperdine)-3,9-dioxo-6-thia-hendecane

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Experimental program
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Effect test

Embodiment 1

[0027] (1) Add 3.2g (0.08mol) of NaOH and 10ml of DMF into a reaction flask equipped with a stirrer and a thermometer, add 1.22g (0.01mol) of thiodiglycol under stirring, and then add N in batches within 0.5 hours - Chloroethylpiperidine hydrochloride 4.6g (0.025mol), react at 70°C for 5 hours after addition;

[0028] (2) After the above reaction is completed, cool the reaction solution to room temperature, add 15ml of water to stir, extract with 15ml of ethyl acetate, wash with water, and wash with anhydrous MgSO 4 Concentrate after drying, and distill under reduced pressure at 195°C / 0.098Mpa to obtain 1.92g of light yellow liquid 1,11-bis(1-bispiperidine)-3,9-dioxo-6-thia-undecane , yield 56.8%, gas chromatography purity 97.6%.

Embodiment 2

[0030] (1) Add 4.0g (0.1mol) of NaOH and 15ml of DMF into a reaction flask equipped with a stirrer and a thermometer, add 1.22g (0.01mol) of thiodiethylene glycol under stirring, and then add N in batches within 0.8 hours - Chloroethylpiperidine hydrochloride 5.52g (0.03mol), react at 60°C for 6 hours after addition;

[0031] (2) After the above reaction is completed, cool the reaction solution to room temperature, add 305ml of water and stir, extract with 25ml of ethyl acetate, wash with water, and wash with anhydrous MgSO 4 Concentrate after drying, and distill under reduced pressure at 190℃ / 0.01Mpa to obtain 1.92g of light yellow liquid 1,11-bis(1-bispiperidine)-3,9-dioxo-6-thia-undecane , yield 57.2%, gas chromatography purity 98%.

Embodiment 3

[0033] (1) Add 4.0g (0.1mol) of NaOH and 20ml of DMF into a reaction flask equipped with a stirrer and a thermometer, add 1.22g (0.01mol) of thiodiethylene glycol under stirring, and then add N in batches within 1.0 hours - Chloroethylpiperidine hydrochloride 5.52g (0.03mol), react at 70°C for 6 hours after addition;

[0034] (2) After the above reaction is completed, cool the reaction solution to room temperature, add 20ml of water and stir, extract with 30ml of ethyl acetate, wash with water, and wash with anhydrous MgSO 4 Concentrate after drying, and distill under reduced pressure at 200℃ / 0.099Mpa to obtain 1.92g of light yellow liquid 1,11-bis(1-bispiperidine)-3,9-dioxo-6-thia-undecane , yield 57.6%, gas chromatography purity 98.5%.

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Abstract

The invention provides a preparation method of 1,11-di(1-bispiperdine)-3,9-dioxo-6-thia-hendecane. The preparation method comprises the following steps of: (1) adding N,N-dimethylformamide and sodium hydroxide to a reaction container, adding thiodiglycol under stirring at a room temperature, wherein the mol ratio of the thiodiglycol to the sodium hydroxide is 1: (4-12); adding N-chloroethyl piperidine hydrochloride in batches in 0.5-1 hour, wherein the mol ratio of the thiodiglycol to the N-chloroethyl piperidine hydrochloride is 1: (2-4); and reacting for 3-8 hours at a reaction temperature in the range from 40 to 90 DEG C; (2) cooling after the reaction is completed until the temperature reaches the room temperature, adding water and stirring, extracting by using a solvent, washing with water, drying and concentrating, and then performing reduced pressure distillation, thereby obtaining the 1,11-di(1-bispiperdine)-3,9-dioxo-6-thia-hendecane. The preparation method provided by the invention is simple in steps, short in reaction time, simple in after-treatment process, high in yield, low in cost, and convenient for industrial production.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to a preparation method of 1,11-bis(1-bispiperidine)-3,9-dioxo-6-thia-undecane. Background technique: [0002] Japanese Patent JP Patent Publication Hei 7-13284 discloses the preparation method of 1,11-bis(1-bispiperidine)-3,9-dioxo-6-thia-undecane: [0003] [0004] The reaction steps of the method are as follows: first neutralize and desalt N-chloroethylpiperidine hydrochloride with aqueous sodium hydroxide solution, extract and concentrate with dichloromethane to obtain N-chloroethylpiperidine, and then use sodium hydride to bind The acid agent reacts with thiodiethylene glycol, pours into water, extracts and concentrates with ethyl acetate to obtain a crude product, dissolves in hydrochloric acid and treats it with n-hexane, then neutralizes with alkali, extracts and concentrates with ethyl acetate, and distills under reduced pressure to prepare 1,11-bis(1-bispiperidine)-3,9-di...

Claims

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Application Information

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IPC IPC(8): C07D295/088
Inventor 初虹成志秀滕领贞
Owner 沈阳感光化工研究院有限公司
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