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Method for preparing beta-aminoketone, ester and nitrile amide derivatives

A technology of nitrile, amide and amino ketone, applied in the field of beta-amino ketone, nitrile and amide derivatives, and ester, can solve the problems of poor catalyst reuse and small selection range, and achieve good reusability, low price, The effect of mild reaction conditions

Inactive Publication Date: 2013-09-18
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these reaction systems require excess reagents or the substrate selection range of some catalysts is small or the reusability of some catalysts is poor and the use of some toxic and harmful solvents (1,2-dichloroethane and acetonitrile)

Method used

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  • Method for preparing beta-aminoketone, ester and nitrile amide derivatives
  • Method for preparing beta-aminoketone, ester and nitrile amide derivatives
  • Method for preparing beta-aminoketone, ester and nitrile amide derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add morpholine (5mmol), methyl acrylate (5.5mmol), and 1mmol ionic liquid [Ch][OMe] into a 50mL single-necked bottle in turn, stir at room temperature for 0.5 hours, TLC detection, the raw materials disappear, extract the reaction solution with ether, and combine The organic phase was separated by column chromatography to obtain the product with a yield of 96% and a content of 98%.

[0023] 3-(1-Morpholinyl)-propionic acid methyl ester: 1 H NMR (400MHz, CDCl 3 )(ppm):3.66(s,3H,OCH 3 ),3.67-3.65(m,4H,morpholinyl),2.65(t,2H,J=6Hz,CH 2 ),2.48(t,2H,J=6Hz,CH 2 ),2.43-2.41(m,4H,morpholinyl); 13 C NMR (100MHz, CDCl 3 )(ppm): 172.8, 66.8, 53.8, 53.3, 51.6, 31.7.

Embodiment 2

[0025] Add n-propylamine (5mmol), methyl acrylate (10mmol), and 5mmol ionic liquid [Ch][OMe] into a 50mL single-necked bottle in sequence, stir at room temperature for 0.5 hours, TLC detects that the raw materials disappear, extract the reaction solution with ether, and combine the organic Phase, column chromatography separation to obtain the product, the yield is 91%, and the content is 98%.

[0026] 3-(1-Propylamine)-propionic acid methyl ester: 1 H NMR (400MHz, CDCl 3 )(ppm):3.63(s,3H,OCH 3 ),2.62(t,2H,J=6.4Hz,CH 2 ),2.45(t,2H,J=6.4Hz,CH 2 ),2.58(m,2H,CH 2 ),1.41(m,2H,CH 2 ),0.90(m,3H,CH 3 ); 13 C NMR (100MHz, CDCl 3 )(ppm): 170.5, 66.8, 52.8, 52.1, 44.9, 28.1, 12.3.

Embodiment 3

[0028] Add piperidine (5mmol), methyl acrylate (5.5mmol), and 1mmol ionic liquid [Ch][OMe] into a 50mL single-necked bottle in turn, stir at room temperature for 0.5 hours, TLC detection, the raw materials disappear, extract the reaction solution with ether, and combine The organic phase was separated by column chromatography to obtain the product with a yield of 96% and a content of 99%.

[0029] 3-(1-Piperidinyl)-propionic acid methyl ester: 1 H NMR (400MHz, CDCl 3 )(ppm):3.86(s,3H,OCH 3 ),2.86(t,2H,J=6Hz,CH 2 ),2.68(t,2H,J=6Hz,CH 2 ),1.80-1.75(m,4H,piperidinyl),1.61-1.44(m,4H,piperidiny),1.42-1.26(m,2H,piperidinyl); 13 C NMR (100MHz, CDCl 3 )(ppm): 173.8, 54.2, 53.8, 52.9, 31.8, 29.3, 25.8, 24.6, 23.1.

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Abstract

The invention discloses a method for preparing beta-aminoketone, ester and nitrile amide derivatives. The method comprises the steps of: by taking choline chloride functional ionic liquid as a catalyst, carrying out aza-Michael addition reaction on an amine substance and electron-deficient olefins at room temperature and normal pressure, so as to obtain the beta-aminoketone, ester, nitrile amide derivatives. The choline chloride functional ionic liquid can be repeatedly utilized for a plurality of times. The method is simple to operate, high in yield, good in reusability of a catalytic reaction system and mild in reaction condition, and has a good industrial prospect.

Description

technical field [0001] The invention discloses an efficient and green method for preparing β-aminoketone, ester, nitrile and amide derivatives through Michael addition reaction using choline chloride functional ionic liquid as a catalyst. Background technique [0002] β-Amino ketone, ester, nitrile and amide derivatives are widely used as intermediates in the fields of fine chemical industry and antibiotic medicine. General synthetic methods include Mannich reaction and aza-Michael addition. In contrast, Michael addition is more suitable for the preparation of β-amino ketones, esters, nitriles and amides derivatives. Over the years, many catalysts have emerged, such as: LiClO 4 ,Yb(OTf 3 ), Bi(NO 3 ), FeCl 3 .6H 2 O, CeCl 3 .7H 2 O,InCl 3 , SmI 2 and Cu(OTf) 2 Wait. In recent years, a number of new catalytic reaction systems have emerged, such as β-cyclodextrin, Bromodimethylsulfonium bromide, Boric acid in water, ZrOCl 2 .8H 2 O onmontmorillonite K10,Imidazoli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/15C07C229/12C07C229/18C07C227/06C07D233/56C07C225/06C07C221/00C07D295/116B01J31/02
Inventor 应安国武承林李嵘嵘杭智军杨圆
Owner TAIZHOU UNIV
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