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Synthesis method for alpha-carbonylamide compound

A technology of carbonyl amides and synthesis methods, which is applied in the field of synthesis of N-substituted α-carbonyl amides, can solve the problems of high toxicity of reaction raw materials or oxidants, difficulty in obtaining raw materials, harsh reaction conditions, etc., and achieve mild conditions and easy raw materials. Get and respond to the effect of high efficiency

Inactive Publication Date: 2008-02-13
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] In summary, there are many methods for preparing α-carbonyl amides, but the raw materials for these reactions are not easy to obtain, and need to go through relatively complicated synthesis steps; the reaction raw materials or oxidants used in some reactions are more toxic and easy to cause environmental pollution ; The yield of some reactions is relatively low or the reaction conditions are relatively harsh, etc.

Method used

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  • Synthesis method for alpha-carbonylamide compound
  • Synthesis method for alpha-carbonylamide compound
  • Synthesis method for alpha-carbonylamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of 1-phenyl-2-piperidinyl-1,2-ethyldione

[0028] The preparation of 1-phenyl-2-piperidinyl-1,2-ethyl diketone adopts the following steps: 1. add 10 gram N-piperidinyl phenylacetamides, 1.6 gram cesium carbonate in 250 ml round bottom flask , 1.6 grams of tetrabutylammonium bromide, 100 milliliters of DMF, put in a drying tube and heat to 120 ° C, follow the reaction with thin layer chromatography until the reaction raw material N-piperidinyl phenylacetamide disappears; An appropriate amount of ethyl acetate was added to the system to dilute the reaction, and then the alkali and additives were filtered out. The crude product was obtained after removing the solvent in the filtrate with a rotary evaporator; ③ the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate=5: 1) to obtain 9.9 grams of light yellow solid, namely 1-phenyl- 2-Piperidinyl-1,2-ethyldione, 93% yield. Melting point: 104-105°C.

[0029] ...

Embodiment 2

[0033] Example 2: Preparation of 1-p-methoxyphenyl-2-piperidinyl-1,2-ethyldione

[0034] The preparation of 1-p-methoxyphenyl-2-piperidinyl-1,2-ethyldiketone adopts the following steps: 1. add 7 grams of N-piperidinyl-p-methoxyl in a 250 ml round bottom flask Phenylphenylacetamide, 1.2 grams of cesium carbonate, 3.3 grams of tetrabutylammonium bisulfate, 100 milliliters of DMF, heated to 120 ° C after installing a drying tube, followed the reaction by thin layer chromatography, until the reaction raw material N-piperidinyl- p-methoxyphenylacetamide disappeared; ②After the reaction, add an appropriate amount of ethyl acetate to the system to dilute the reaction, and then filter out the alkali and additives. The crude product was obtained after removing the solvent in the filtrate with a rotary evaporator; ③ the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1) to obtain 6.8 grams of light yellow liquid, which was 1-p-methoxy ...

Embodiment 3

[0039] Example 3: Preparation of 1-p-nitrophenyl-2-piperidinyl-1,2-ethyldione

[0040] The preparation of 1-p-nitrophenyl-2-piperidinyl-1,2-ethyldiketone adopts the following steps: 1. add 7 grams of N-piperidinyl-p-nitrobenzene in a 250 ml round bottom flask Acetamide, 1.9 grams of cesium carbonate, 1.8 grams of tetrabutylammonium iodide, 100 milliliters of DMF, put in a drying tube and heat to 100-120 ° C, follow the reaction by thin layer chromatography until the reaction raw material N-piperidinyl- p-Nitrophenylacetamide disappears; ②After the reaction, add an appropriate amount of ethyl acetate to the system to dilute the reaction, and then filter out the alkali and additives. The crude product was obtained after removing the solvent in the filtrate with a rotary evaporator; ③ the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 3: 1) to obtain 4.8 grams of a light yellow solid, which was 1-p-nitro Phenyl-2-piperidinyl-1,2-...

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Abstract

The invention relates to a synthesis method for the alpha-carbonyl amide compound. The specific steps of the method are: dissolve the amide, the carbonic cesium of the amount of the catalyst and the additive of the amount of the catalyst into the DMF and communicate the solution with the air through the drying pipe; at the temperature of 100 to 120 Celsius system, the material is heated and reacted until the raw material amide disappears; the ethyl acetate is added into the reaction system to dilute; then the method is to filter to remove the solvent in the filter liquid and to get the crude product; after the purification, the required alpha-carbonyl amide can be got. The raw material of the invention is easy to get; the operation is quite simple; the conditions are mild; the invention is suitable for the large-scale industrial production; the air is used as the green oxidant; the reaction is of the environmental protection, and highly efficient; the production rate can reach to 93 percent.

Description

technical field [0001] The invention relates to a synthesis method of α-carbonyl amide compounds, in particular to a synthesis method of N-substituted α-carbonyl amide compounds. Background technique [0002] α-Carbonylamides play a very important role in organic chemistry and medicinal chemistry. This type of compound itself has strong physiological activities, such as anti-virus, inhibitor of various enzymes and receptors, treatment of muscular dystrophy, etc., and some natural products such as indigo and FK506 contain this kind of molecular skeleton. In addition, it is also a very important synthetic intermediate. FK506, which contains α-carbonyl amide skeleton, extracted from Streptomyces, can be used to suppress the immunity of organisms on the one hand, and can be used for protein synthesis in vivo on the other hand. It has attracted more and more attention in recent years. The α-carbonyl amide is an important synthetic precursor for the synthesis of FK506. [0003]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/32C07D401/04C07C235/80
Inventor 许斌王思远宋炳瑞饶薇薇
Owner SHANGHAI UNIV
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