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Pyrrolidine ionic compounds containing phenoxy substituents, and preparation method thereof

An ionic compound, methylpyrrolidine technology, applied in the field of preparation of the aforementioned pyrrolidine ionic compound, can solve the problem of not finding that pyrrolidine cations are introduced into phenylalkyl substituents and the like

Inactive Publication Date: 2011-11-23
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, various N, N'-dihydrocarbyl substituted imidazole ionic liquids have been reported, especially the introduction of a C 1 ~C 6 Alkylene substituent and a C 1 ~C 6 N, N'-dihydrocarbyl substituted imidazole ionic liquids of disubstituted phenyl groups with alkyl, nitro or halogen substituents, but no report on the introduction of phenylalkyl substituents on pyrrolidinium cations was found

Method used

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  • Pyrrolidine ionic compounds containing phenoxy substituents, and preparation method thereof
  • Pyrrolidine ionic compounds containing phenoxy substituents, and preparation method thereof
  • Pyrrolidine ionic compounds containing phenoxy substituents, and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0094] Example 1 :Synthesis of N-(2-nitrobenzyl)-N-methylpyrrolidine bromide

[0095]

[0096] Weigh 10.80g (50mmol) of 2-nitrobenzyl bromide and 4.26g (50mmol) of N-methylpyrrolidine and dissolve them in 50mL (0.50mol) of ethyl acetate to prepare a solution. Under stirring conditions, the ethyl acetate solution of 2-nitrobenzyl bromide was slowly added dropwise to the ethyl acetate solution of N-methylpyrrolidine, and the reaction was stirred at room temperature for 8 hours. The solid product was separated by filtration, and the solid product was washed 8 times with freshly distilled ethyl acetate, with an amount of 20 mL each time, and then vacuum dried to remove volatile components to obtain an off-white solid powder. The obtained product was confirmed to be the compound described in the title by infrared spectroscopy and nuclear magnetic resonance spectroscopy, and the yield was 98%. FTIR(cm -1 ): 3465, 3391, 3032, 3015, 1605, 1575, 1527, 1480, 1457, 1348, 1007, 935, 915, 8...

Embodiment 2

[0097] Example 2 :Synthesis of N-(3-nitrobenzyl)-N-methylpyrrolidine bromide

[0098]

[0099] Weigh 10.80g (50mmol) of 3-nitrobenzyl bromide and dissolve it in 25mL (0.25mol) of ethyl acetate to make a solution. Weigh 4.26g (50mmol) of N-methylpyrrolidine and dissolve in 70mL (0.70mol) of acetic acid Make a solution in ethyl ester. Under stirring conditions, the ethyl acetate solution of 3-nitrobenzyl bromide was slowly added dropwise to the ethyl acetate solution of N-methylpyrrolidine, and the reaction was stirred at room temperature for 8 hours. The solid product was separated by filtration, and the solid product was washed 8 times with freshly distilled ethyl acetate, with an amount of 20 mL each time, and then vacuum dried to remove volatile components to obtain an off-white solid powder. The obtained product was confirmed by infrared spectrum and nuclear magnetic resonance spectrum analysis to be the compound described in the title, and the yield was 93%. FTIR(cm -1 ): ...

Embodiment 3

[0100] Example 3 :Synthesis of N-(4-nitrobenzyl)-N-methylpyrrolidine bromide

[0101]

[0102] Weigh 10.80g (50mmol) of 4-nitrobenzyl bromide and dissolve it in 30mL (0.30mol) ethyl acetate to make a solution. Weigh 4.26g (50mmol) of N-methylpyrrolidine and dissolve in 50mL (0.50mol) Make a solution in ethyl acetate. Under stirring conditions, the ethyl acetate solution of 4-nitrobenzyl bromide was slowly added dropwise to the ethyl acetate solution of N-methylpyrrolidine, and the reaction was stirred at room temperature for 8 hours. The solid product was separated by filtration, and the solid product was washed 8 times with freshly distilled ethyl acetate, with an amount of 20 mL each time, and then vacuum dried to remove the volatile components to obtain a light yellow solid powder. The obtained product was confirmed to be the compound described in the title by infrared spectroscopy and nuclear magnetic resonance spectroscopy, and the yield was 95%. FTIR(cm -1 ): 3038, 3007,...

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Abstract

The invention relates to pyrrolidine ionic compounds A<+>B<->. A<+> is represented by a formula (I), wherein R1 is hydrocarbonyl containing 1 to 6 carbon atoms. R2 has a structure represented by a formula (II), wherein n is an integer from 1 to 6, and Y is H, C1 to C6 alkyl or nitro. * represents a connection between the structure of the formula (II) and a nitrogen atom in the formula (I). B<-> is Cl<->, Br<->, I<->, NO3<->, SO4<->, PO4<->, BF4<->, PF6<->, [(CF3SO2)2N] <->, Ac<->, [CH3C6H4SO3]<-> or [CF3SO3]<->. The invention also relates to a preparation method of A<+>B<-> pyrrolidine ionic compounds. The method comprises the steps that: compounds represented by a formula (III) are subject to compounds represented by a formula (IV), such that halide pyrrolidine ionic compounds A<+>B<->, in which B<-> is Cl<->, Br<-> or I<->, are obtained. Pyrrolidine ionic compounds containing other anions can be obtained through ion replacements upon the halide pyrrolidine ionic compounds. The halide pyrrolidine ionic compounds provided by the invention can be used as solvents or catalysts used in fields of organic synthesis, high-molecular synthesis, high-molecular processing, and the like.

Description

Technical field [0001] The present invention relates to a pyrrolidine ionic compound, in particular to a pyrrolidine ionic compound containing a phenylalkyl substituent, which can be used as an ionic liquid. The present invention also relates to a method for preparing the aforementioned pyrrolidine ion compound. Background technique [0002] The ionic liquid refers to an organic molten salt composed of a specific asymmetric organic cation with a relatively large volume and an inorganic or organic anion with a relatively small volume. Compared with traditional liquid substances (molecular solvents), ionic liquids are ionic compounds. Therefore, ionic liquids often exhibit unique properties and unique functions, and are a new type of "soft" functional material or medium with application potential. [0003] When used as a solvent, compared to traditional solvents, ionic liquids have the following advantages: almost no vapor pressure, non-flammable, and high thermal stability. The ph...

Claims

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Application Information

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IPC IPC(8): C07D295/073C07D295/037C07D295/023C08G63/81
Inventor 刘正平窦军彦
Owner BEIJING NORMAL UNIVERSITY