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2-morpholinone salt and preparation method thereof, and preparation method of 2-morpholinone

A technology of morpholinone salt and morpholinone, applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of complex synthesis process of 2-morpholinone, unfavorable large-scale production, complex reaction process, etc., so as to avoid difficulty in separation and collection. The effect of increased rate and simple response

Inactive Publication Date: 2020-09-11
HUANGHUAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the prior art, the synthesis process of 2-morpholinone is generally more complicated, and the cost of raw materials is higher, and the yield is lower, which is not conducive to large-scale production
Such as "Oxidant-Free Conversion of Cyclic Amines to Lactams andH 2 Using Water As the Oxygen Atom Source "(JACS, Julia R etc., 2014.2) discloses a kind of synthetic process of 2-morpholinone, when synthesizing 2-morpholinone in this method, reaction process is complicated, and efficiency is low

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  • 2-morpholinone salt and preparation method thereof, and preparation method of 2-morpholinone

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preparation example Construction

[0093] The synthetic route of the preparation method of 2-morpholinone of the present invention:

[0094]

Embodiment 1

[0096] The preparation method of the 2-morpholinone salt of the present embodiment may further comprise the steps:

[0097] 1) Add 2000mL of water, 149g (2mol) of glyoxylic acid, 122g (2mol) of ethanolamine, and palladium-carbon composite material (8g) into a single-necked bottle with a stirrer, wherein the mass fraction of palladium in the palladium-carbon composite material is 10% After stirring and mixing evenly, heat to 40 ° C, hydrogenation reduction reaction at normal pressure for 24 hours, after the reaction, cool to room temperature; filter, the filter residue is a palladium-carbon composite material, the filtrate is concentrated to dryness, and then recrystallized with ethanol to obtain N-( 2-Hydroxyethyl)glycine (230 g); 97% yield.

[0098] 2) At room temperature, add 1000mL dioxane, 500mL water, 80g (2mol) sodium hydroxide, 238g (2mol) N-(2-hydroxy Ethyl) glycine, stirred for 0.5h, slowly added dropwise 340g (2mol) benzyl chloroformate, and reacted at room temperat...

Embodiment 2

[0105] The preparation method of the 2-morpholinone salt of the present embodiment may further comprise the steps:

[0106] 1) Add 2000mL of water, 149g (2mol) of glyoxylic acid, 122g (2mol) of ethanolamine, and palladium-carbon composite material (8g) in a single-necked bottle with a stirrer, wherein the mass fraction of palladium in the palladium-carbon composite material is 10% ; Stir and mix evenly, heat to 40 ° C, hydrogenation reduction reaction at normal pressure for 24 hours, after the reaction, cool to room temperature; filter, the filter residue is a palladium-carbon composite material, the filtrate is concentrated to dryness, and then recrystallized with ethanol to obtain N- (2-Hydroxyethyl)glycine (230 g); 97% yield.

[0107] 2) Add 1000mL of dioxane, 500mL of purified water, 80g (2mol) of sodium hydroxide, 238g (2mol) of N-(2-hydroxyethyl) prepared in step 1) into a three-necked flask with a mechanical stirrer Glycine, add and stir for 0.5h, slowly add 536g (2mol...

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Abstract

The invention relates to a 2-morpholone salt and preparation method thereof, and 2-morpholone preparation method thereof, which belongs to the technical field of synthesis of a drug intermediate. Thepreparation method comprises the following steps: N-(2-hydroxyethyl)glycine with an amino protective group and a catalyst are subjected to a heating backflow reaction in a backflow solvent to preparethe 2-morpholone having the amino protective group; the catalyst is toluenesulfonic acid or concentrated sulfuric acid, and the 2-morpholone having the amino protective group is subjected to acidifying to remove the protective group to obtain the 2-morpholone salt. The 2-morpholone is obtained by reacting the 2-morpholone salt and alkali in the solvent. During the preparation method of 2-morpholone salt and 2-morpholone, the raw materials have the advantages of low cost and easy acquisition, the synthesis route is short, and all reaction intermediates and a final product do not require columnchromatography purifying. The method has the advantages of low cost and high efficiency, and the purity of the product is high.

Description

technical field [0001] The invention relates to a 2-morpholone salt and a preparation method thereof, and a preparation method of 2-morpholone, belonging to the technical field of synthesis of pharmaceutical intermediates. Background technique [0002] 2-Morpholinone is a colorless oily liquid with the molecular formula C 4 h 7 NO 2 , the molecular weight is 101.05. Its hydrochloride is a crystalline white powder with the molecular formula C 4 h 8 ClNO 2 , with a molecular weight of 137.02. In the prior art, 2-morpholinone, as an important pharmaceutical intermediate, is mainly used in the synthesis of quinazoline drugs, which are mainly used in the treatment of cancer. [0003] In the prior art, the synthesis process of 2-morpholinone is generally complicated, and the cost of raw materials is high, and the yield is low, which is not conducive to large-scale production. Such as "Oxidant-Free Conversion of Cyclic Amines to Lactams andH 2 Using Water As the Oxygen Ato...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/32
CPCC07D265/32Y02P20/55
Inventor 王胜强李洋王妍芳胡鹏裴青蓝
Owner HUANGHUAI UNIV