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6-aryloxymethyl-4-aryl-3-morpholone derivative and its preparation method

A technology of methyl and alkoxy groups, applied in the field of 3-morpholinone derivatives and their preparation

Inactive Publication Date: 2006-02-22
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] For the deficiencies of heterocyclic compounds and preparation methods thereof in existing 3-morpholinone derivatives, the object of the present invention is to provide a kind of 6-aryloxymethyl-4-aryl-3-morpholinone and its synthesis, Separation and purification method

Method used

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  • 6-aryloxymethyl-4-aryl-3-morpholone derivative and its preparation method

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Embodiment 1

[0032] Embodiment 1: Preparation of 6-phenoxymethyl-4-phenylmorpholin-3-one

[0033] 1) Add 3 g (0.020 mol) of 3-phenoxy-1,2-epoxypropane into 30 ml of tetrahydrofuran, then add 2.05 g (0.022 mol) of aniline, then add 12 g of alumina and stir to reflux for 6 hours. Cool to room temperature, separate the alumina by filtration, evaporate tetrahydrofuran under elevated temperature and reduced pressure, and separate the residue by silica gel column chromatography (petroleum ether / ethyl acetate = 2:1, volume ratio) to obtain the aminoalcohol compound 1-benzene Oxy-3-anilino-isopropanol (2.43 g), 50% yield.

[0034] 2) 0.49 grams (0.002 moles) of 1-phenoxy-3-phenylamino-isopropanol was added to 5 milliliters of tetrahydrofuran, then 0.30 grams (0.0022 moles) of potassium carbonate was added, and then 0.25 grams (0.0022 moles) of ) chloroacetyl chloride, after continuing to react under ice bath for 2 hours, the tetrahydrofuran was distilled off under reduced pressure, the remaining ...

Embodiment 2

[0046] Embodiment 2: Preparation of 6-(4-chlorophenoxy)methyl-4-phenylmorpholin-3-one

[0047] 1) Add 3.69 grams (0.020 moles) of 3-(4-chlorophenoxy)-1,2-epoxypropane into 30 milliliters of tetrahydrofuran, then add 2.79 grams (0.030 moles) of aniline, then add 12 grams of alumina and stir Reflux for 6 hours. Cool to room temperature, separate the alumina by filtration, evaporate tetrahydrofuran under elevated temperature and reduced pressure, and separate the residue by silica gel column chromatography (developing solvent is petroleum ether / ethyl acetate=2:1, volume ratio) to obtain the aminoalcohol compound 1-( 4-Chlorophenoxy)-3-phenylamino-isopropanol (2.39 g), 43% yield.

[0048] 2) Add 0.56 grams (0.002 moles) of 1-(4-chlorophenoxy)-3-phenylamino-isopropanol to 5 milliliters of tetrahydrofuran, then add 0.32 grams (0.003 moles) of sodium carbonate, and then add 0.25 g (0.0022 moles) of chloroacetyl chloride, after continuing to react in an ice bath for 2 hours, the tet...

Embodiment 3

[0059] Embodiment 3: Preparation of 6-(4-nitrophenoxy)methyl-4-phenylmorpholin-3-one

[0060] 1) Add 3.9 grams (0.020 moles) of 3-(4-nitrophenoxy)-1,2-epoxypropane to 30 milliliters of tetrahydrofuran, then add 2.23 grams (0.022 moles) of aniline, and then add 12 grams of alumina Stir and reflux for 6 hours. Cool to room temperature, separate alumina by filtration, distill THF under reduced pressure, and separate the residue by silica gel column chromatography (developing solvent is petroleum ether / ethyl acetate=2:1, volume ratio) to obtain aminoalcohol compound 1-(4 -Nitrophenoxy)-3-anilino-isopropanol (3.52 g), yield 61%.

[0061] 2) Add 0.58 grams (0.002 moles) of 1-(4-nitrophenoxy)-3-phenylamino-isopropanol to 5 milliliters of tetrahydrofuran, then add 0.30 grams (0.0022 moles) of potassium carbonate, and then Add 0.25 g (0.0022 moles) of chloroacetyl chloride, continue to react under ice bath for 2 hours, distill off THF under reduced pressure, cool the remaining mixtur...

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Abstract

The invention relates to 6-aryloxy-4-aryl-3-morpholone having a structural formula (I), wherein Z represents O or S, X is H, C1-C4 alkyl, alkoxy, halogen, Y is H, C1-C4 alkyl, alkoxy, halogen, or nitro. The invention also discloses the process for preparing the compound, which comprises reacting 3-aryloxy-1,2-epoxypropane with arylamine compound at the presence of alumina catalysis, then reacting the obtained beta-amino alcohol derivative with chloracetyl chloride under the condition of ice bath, thus obtaining 2-chloro-N-(2-hydroxyl-3-aryloxypropyl)-N-aryl acetamide, finally proceeding self-ring closing at the presence of sodium hydrogenate.

Description

technical field [0001] The invention relates to 3-morpholinone derivatives and a preparation method thereof, in particular to 6-aryloxymethyl-4-aryl-3-morpholinone and its synthesis, separation and purification methods. Background technique [0002] Morpholinone derivatives are an important compound. People have been very interested in this kind of structural compounds, especially the 2-morpholinone derivatives have been extensively explored. The biological activity of the synthesized 2-morpholinone derivatives shows that the derivatives have pharmacological activities such as anti-hyperlipidemia, lowering cholesterol, treating arteriosclerosis and anti-inflammation. For example, the patent No. is ZA7603334, US4237132, JP52083676, JP51146479, US3840536, US20030212062A1 involved in the structure of 2-morpholinone derivatives; in addition, there are patents such as CN1479729A, US6140326 involving 2-morpholinone derivatives as light stabilizers Applications. However, there a...

Claims

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Application Information

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IPC IPC(8): C07D265/32
Inventor 赵宝祥谭伟
Owner SHANDONG UNIV
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