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2, 2'-bi-pyridine amine copper complex and application thereof in 2-imidazoline derivative synthesis

A technology of copper complexes and complexes, applied in the direction of copper organic compounds, organic compounds/hydrides/coordination complex catalysts, chemical/physical processes, etc., can solve serious environmental pollution, low yield, long reaction time, etc. problems, to achieve the effect of simple preparation process, less dosage, and little influence on separation

Inactive Publication Date: 2013-07-17
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the process is simple, the reaction time is long, the yield is low, and a large number of corrosive raw materials are used, causing serious environmental pollution.

Method used

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  • 2, 2'-bi-pyridine amine copper complex and application thereof in 2-imidazoline derivative synthesis
  • 2, 2'-bi-pyridine amine copper complex and application thereof in 2-imidazoline derivative synthesis
  • 2, 2'-bi-pyridine amine copper complex and application thereof in 2-imidazoline derivative synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: Synthesis of complexes shown in structural formula (I)

[0021] Weigh 0.20g of copper acetate and 0.17g of 2,2'-dipyridylamine, dissolve in 100mL of methanol:water (V / V)=1:1 solution, add formic acid dropwise to adjust the pH value to 5, heat to reflux for 2h, Filter the clear liquid in a Erlenmeyer flask, cool and crystallize to obtain the product. The test data of the single crystal structure is: Molecular formula C 54 h 49 Cu 2 N 15 o 8 , which belongs to the monoclinic crystal system, Cc space group, and the unit cell parameters are a = 11.5409(7)?, b = 15.3626(9)?, c = 30.2072(18)?, α = 90 (deg), β =90.4940(10) deg, gamma = 90 deg.

Embodiment 2

[0022] Embodiment 2: Synthesize 2-phenylimidazoline with benzonitrile and ethylenediamine as raw materials.

[0023] Add 5mmol of benzonitrile, 20mmol of ethylenediamine and 1mmol of the catalyst prepared in Example 1 into a 50mL round bottom flask, and heat to reflux for 6h under stirring. After the reaction is complete, add 20 mL of CH 2 Cl 2 , after filtering off the catalyst, the CH 2 Cl 2 Evaporate to dryness to obtain 2-phenylimidazoline crude product, column separation (eluent: ethyl acetate / methanol (V / V)=3:1) obtains 2-phenylimidazoline pure product 0.63g, yield is 86 %. Mass Spectrum (m / z): 147 [M+H] + . NMR: 1 H NMR (400MHz, CDCl 3 ): δ 3.78 (s, 4H, 2CH 2 ), 4.78 (br s, 1H, NH), 7.39-7.45 (m, 3H, ArH), 7.76-7.80 (m, 2H, ArH). Infrared (KBr): ν / cm -1 : 3201, 2929, 2867, 1611, 1571, 1508, 1469, 1344, 1269, 981, 778, 696.

Embodiment 3

[0024] Embodiment 3: take p-chlorobenzonitrile and ethylenediamine as raw material synthesis 2-(p-chlorophenyl) imidazoline

[0025] Add 5mmol of p-chlorobenzonitrile, 20mmol of ethylenediamine and 1mmol of the catalyst prepared in Example 1 into a 50mL round bottom flask, and heat to reflux for 6h under stirring. After the reaction is complete, add 20 mL of CH 2 Cl 2 , after filtering off the catalyst, the CH 2 Cl 2 Evaporate to dryness to obtain 2-(p-chlorophenyl) imidazoline crude product, column separation (eluent: ethyl acetate / methanol (V / V)=3:1) obtains 2-(p-chlorophenyl) imidazoline pure Product 0.70g, the yield is 78%. Mass Spectrum (m / z): 181 [M+H] + . NMR: 1 H NMR (CDCl 3, 400MHz) δ: 3.80 (s, 4H, 2CH 2 ), 7.38 (d, 2H, ArH), 7.73 (d, 2H, ArH). Infrared (KBr): ν / cm -1 : 3235, 2697, 2361, 1605, 1558, 1518, 1483, 1351, 1274, 1125, 1089, 986, 838, 727.

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Abstract

The invention discloses a complex shown by a structural formula (I). The complex is obtained by adding formic acid into soluble copper salt and 2, 2'-pyridine amine to adjust pH value to 5, heating and refluxing. The complex can be taken as a catalyst to be used for synthesis of 2-imidazoline and derivatives thereof, and has the advantages of mild reaction condition, high yield, short reaction time, simplicity and convenience in post-treatment, low catalyst price, reusability, freeness of solvent interference, and the like.

Description

technical field [0001] The invention relates to a 2,2'-dipyridylamine copper complex and its application as a catalyst in the synthesis of 2-imidazoline and its derivatives, belonging to the technical field of chemistry and chemical engineering. Background technique [0002] 2-Imidazoline is an important chemical intermediate widely used in organic synthesis, biomedicine, pharmaceutical and other industries. In the field of synthetic chemistry, it can often be used as an intermediate in the synthesis of natural products, designed and synthesized by phase transfer catalysts, and can be used as achiral or chiral catalysts after coordination with transition metals; in the field of biomedicine, 2-imidazoline It can be used as α-adrenergic receptor antagonist, α-adrenergic receptor agonist, etc. In the pharmaceutical industry, 2-imidazoline can be used as the main component of various anti-inflammatory drugs, antihypertensive drugs and anticancer drugs. There are many synthetic ...

Claims

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Application Information

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IPC IPC(8): C07F1/08C07D213/72B01J31/22C07D233/06C07D233/20C07D401/04
Inventor 刘萍张文涛庞鹏张金李剑利
Owner NORTHWEST UNIV
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