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Synthesis method of N,N-dialkyl diphenyl propionamide

A technology of diphenylpropanamide and dialkylacetamide, applied in the field of organic chemical synthesis, to achieve the effect of simple and efficient synthetic route, easy separation, and easy reaction conditions

Active Publication Date: 2018-10-16
山东德静能源科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The invention discloses a method of using metal samarium to promote the coupling reaction of diphenyl ketone and N,N-dialkylacetamide under the catalysis of cuprous iodide to prepare N , the method of N-dialkyldiphenylpropanamide, this method has not yet seen domestic and international bibliographical information

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  • Synthesis method of N,N-dialkyl diphenyl propionamide
  • Synthesis method of N,N-dialkyl diphenyl propionamide

Examples

Experimental program
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Effect test

example 1

[0019] Add 3.6g of benzophenone and 3.6mL of N,N-dimethylacetamide to the dry reaction vessel in sequence, stir and dissolve, then add 0.9g of newly prepared samarium metal powder, 2.6mg of iodide Cuprous, magnetically stirred for 10min. Add 0.5 mL p-toluenesulfonic acid to the reaction system. The reaction was carried out under slight reflux by heating, and the reaction was 3h. The temperature was lowered, the reaction solution was extracted with ethyl acetate, and the crude product of N,N-dialkyldiphenylpropanamide was obtained after post-processing. Then it was further separated by column chromatography and purified by recrystallization to obtain N,N-dialkyldiphenylpropanamide with a yield of 91%.

[0020] N,N-Dimethyl-3,3-diphenylpropanamide, white solid, melting point 105-106℃. 1 HNMR (500MHz, CDCl 3 )δppm 2.8 3-2.92(s,6H),3.02-3.06(d,2H),4.67-4.73(t,1H),7.16-7.21(m,2H),7.22-7.31(m,8H). 13 C NMR (125MHz, CDCl 3 )δppm 144.3, 128.4, 126.3, 77.3, 77.0, 76.8, 47.0, 39.3...

example 2

[0022] According to the method in Example 1, N,N-diethylacetamide was used instead of N,N-dimethylacetamide, and other conditions remained unchanged, to obtain N,N-diethyldiphenylpropanamide with a yield of 87%.

example 3

[0024] According to the method in Example 1, the reaction temperature is room temperature, the reaction time is 8 h, 3 h, and other conditions remain unchanged, to obtain N,N-dimethyldiphenylpropanamide with a yield of 62%.

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Abstract

The invention discloses a synthesis method of N,N-dialkyl diphenyl propionamide. The method is characterized by accelerating coupling reaction of diphenylketone and N,N-dialkyl acetamide under the action of p-toluenesulfonic acid in the absence of solvent by using metallic samarium under the catalysis of cuprous iodide so as to prepare N,N-dialkyl-3,3-diphenyl propionamide. The method comprises the following steps: mixing and dissolving diphenyl ketone in N,N-dialkyl acetamide under stirring, then successively adding metallic samarium powder and cuprous iodide powder; adding p-toluenesulfonicacid, reacting through a reaction system in the absence of water, stirring until the reaction is completed; treating the obtained reaction mixed liquid, then carrying out column chromatography separation to obtain pure N,N-dialkyl-3,3-diphenyl propionamide with a yield of 60-99%.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a method for preparing N,N-dialkyldiphenylpropionamides promoted by metal samarium under a solvent-free condition. Background technique [0002] The full name of N,N-dialkyldiphenylpropanamide is N,N-dialkyl-3,3-diphenylpropanamide, and its chemical structure is as follows: [0003] [0004] N, N-dialkyldiphenylpropanamide is a class of useful intermediates in organic synthesis [document 1.GilbertG.Journal of American Chemical Society, 1955,77 (16): 4413-4415.], in recent years in There are also new applications in terms of derivatives combined with fullerenes [Document 2. Tada T, Ishida Y, Saigo K. The Journal of Organic Chemistry, 2006, 71: 1633-1639.]. In reducing agents such as H 2 , LiAlH 4 Under the action of other reagents, N,N-dialkyldiphenylpropanamide can be reduced to N,N-dialkyldiarylpropylamines with wide biological activity and pharmaceuti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/11C07C231/12
CPCC07C231/12C07C233/11
Inventor 刘永军宋斌齐燕
Owner 山东德静能源科技有限公司
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