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Process for preparing 2-substituted enamine or enoyl amine

An enamide and compound technology, which is applied in the field of preparation of arylalkenylamine compounds, can solve the problems of low yield, complex preparation process, environmental pollution and the like, and achieves the effects of high yield, simple preparation process and little environmental pollution

Inactive Publication Date: 2006-08-23
ZHEJIANG UNIV OF TECH
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  • Description
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Problems solved by technology

[0005] In order to overcome the disadvantages of complex preparation process, low yield and serious environmental pollution in the prior art, the present invention provides a preparation method of 2-substituted enamine or enamide compound

Method used

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  • Process for preparing 2-substituted enamine or enoyl amine
  • Process for preparing 2-substituted enamine or enoyl amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Preparation of 1-[1-(4-acetylphenyl)vinyl]-2-pyrrolidone

[0029] 199 mg (1 mmol) of 4-bromoacetophenone, 9 mg (0.04 mmol) of palladium acetate, 33 mg (0.08 mmol) of 1,3-bis(diphenylphosphine) propane, N-vinyl- 334 mg (3 mmol) of 2-pyrrolidone, 17 mg (0.16 mmol) of triethylamine, 2 ml of 1-butyl-3-methylimidazolium tetrafluoroborate, placed in a 50 ml three-necked flask, stirred and heated , reacted at 110°C for 15 hours. After the reaction was completed, it was cooled, the reaction solution was separated to remove the ionic liquid, and extracted with dichloromethane to obtain 206 mg of the product, with a yield of 90%.

[0030] 1 H NMR (CDCl 3 )δppm: 7.92~7.94(m, 2H), 7.44~7.41(m, 2H), 5.40(s, 1H), 5.30(s, 1H), 3.60(t, J=7.0Hz, 2H), 2.60(s , 3H), 2.58(t, J=7.5Hz, 2H), 2.16(dd, J=7.0, 7.5Hz, 2H);

[0031] 1 3C NMR (CDCl 3 )δppm: 198.8, 174.8, 143.6, 140.6, 137.3, 128.9, 126.9, 110.4, 49.9, 32.5, 27.0, 19.0;

[0032] MS (m / z): 229 (M + ).

Embodiment 2

[0033] Example 2 Preparation of 10[1-(4-fluorophenyl)vinyl]-2-pyrrolidone

[0034] 175 mg (1 mmol) of 4-fluorobromobenzene, 9 mg (0.04 mmol) of palladium acetate, 33 mg (0.08 mmol) of 1,3-bis(diphenylphosphine)propane, N-vinyl-2 - 334 mg (3 mmol) of pyrrolidone, 17 mg (0.16 mmol) of triethylamine, 2 ml of 1-butyl-3-methylimidazolium tetrafluoroborate, placed in a 50 ml three-necked flask, stirred and heated, React at 125°C for 20 hours. After the reaction was completed, it was cooled, the reaction solution was separated to remove the ionic liquid, and extracted with dichloromethane to obtain 180 mg of the product with a yield of 88%.

[0035] 1 H NMR (CDCl 3 )δppm: 7.92~7.94(m, 2H), 7.06~7.01(m, 2H), 5.30(s, 1H), 5.25(s, 1H), 3.55(t, J=7.0Hz, 2H), 2.56(t , J=8.0Hz, 2H), 2.12(dd, J=7.0, 8.0Hz, 2H);

[0036] 13 C NMR (CDCl 3 )δppm: 174.8, 164.8, 162.6, 143.6, 128.3, 115.9, 109.2, 49.9, 32.3, 19.0;

[0037] MS (m / z): 205 (M + ).

Embodiment 3

[0038] Example 3 Preparation of 1-[1-(4-methoxyphenyl)vinyl]-2-pyrrolidone

[0039]187 mg (1 mmol) of 4-bromoanisole, 9 mg (0.04 mmol) of palladium acetate, 33 mg (0.08 mmol) of 1,3-bis(diphenylphosphine)propane, N-vinyl- 334 mg (3 mmol) of 2-pyrrolidone, 17 mg (0.16 mmol) of triethylamine, 2 ml of 1-butyl-3-methylimidazolium tetrafluoroborate, placed in a 50 ml three-necked flask, stirred and heated , reacted at 115°C for 20 hours. After the reaction was completed, it was cooled, the reaction solution was separated to remove the ionic liquid, and extracted with dichloromethane to obtain 198 mg of the product, with a yield of 91%.

[0040] 1 H NMR (CDCl 3 )δppm: 7.06~6.97(m, 2H), 6.75~6.47(m, 2H), 4.98(s, 1H), 4.87(s, 1H), 3.45(s, 3H), 2.19(dd, J=7.0, 8.0Hz, 2H), 2.10(t, J=8.0Hz, 2H), 1.76(m, 2H);

[0041] 13 C NMR (CDCl 3 )δppm: 172.8, 160.8, 143.6, 127.3, 127.0, 126.8, 114.9, 114.3, 107.2, 55.9, 41.5, 32.8, 19.0;

[0042] MS (m / z): 217 (M + ).

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Abstract

The invention discloses a process for preparing 2-substituted enamine or enamide compound, characterized by comprising the following steps: halogenated hydrocarbon reacts with enamine or enamide for 1 hour to 50hours with stirring at 20DEG C-150 DEG C, in the presence of catalyst, ligand and organic amine, to produce product 2-aryl allyl alcohol.

Description

(1) Technical field [0001] The invention relates to a preparation method of an unsaturated amine compound, in particular to a preparation method of an aralkenyl amine compound. (2) Background technology [0002] Terminal olefin compounds with amine groups, substituted amine groups or amide groups (pyrrolidone compounds) are important intermediates of many drugs and are multifunctional compounds that can be used to develop new drugs or modify traditional processes for corresponding drugs , has important academic significance and broad application prospects. [0003] The use of Friedel-Crafts to synthesize terminal olefin compounds with amino groups, substituted amino groups or amido groups (pyrrolidone compounds) has many by-products and poor reaction selectivity, making it difficult to carry out industrial production. The Heck reaction is an important supplement to the Friedel-Crafts reaction. Using this reaction in combination with ionic liquids can solve the recycling of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/12C07C235/34C07C235/28C07C231/12C07C211/21C07C209/68
Inventor 裴文孙莉肖建良
Owner ZHEJIANG UNIV OF TECH
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