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Pyrrolidine ionic compounds containing phenoxy substituents, and preparation method thereof

A technology of ionic compounds and pyrrolidine, which is applied in the field of preparation of the aforementioned pyrrolidine ionic compounds, can solve the problem that pyrrolidine cations are not found to introduce phenylalkyl substituents, etc.

Inactive Publication Date: 2014-04-09
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] 10.80 g (50 mmol) of 2-nitrobenzyl bromide and 4.26 g (50 mmol) of N-methylpyrrolidine were weighed and dissolved in 50 mL (0.50 mol) of ethyl acetate to form a solution. Under the condition of stirring, the ethyl acetate solution of 2-nitrobenzyl bromide was slowly added dropwise into 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, washed 8 times with freshly distilled ethyl acetate, 20 mL each time, and then vacuum-dried to remove volatile components to obtain off-white solid powder. The obtained product was confirmed to be the compound described in the title by infrared spectrum and nuclear magnetic resonance spectrum analysis, and the yield was 98%. FTIR (cm -1 ): 3465, 3391, 3032, 3015, 1605, 1575, 1527, 1480, 1457, 1348, 1007, 935, 915, 860, 792, 753, 711. 1 H...

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 form a solution; weigh 4.26g (50mmol) of N-methylpyrrolidine and dissolve it in 70mL (0.70mol) of acetic acid solution in ethyl ester. Under the condition of stirring, 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, washed 8 times with freshly distilled ethyl acetate, 20 mL each time, and then vacuum-dried to remove volatile components to obtain off-white solid powder. The obtained product was confirmed to be the compound described in the title by infrared spectrum and nuclear magnetic resonance spectrum analysis, and the yield was 93%. FTIR (cm -1 ): 3069, 3003, 2960, 2892, 1532, 1474,...

Embodiment 3

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

[0101]

[0102] Weigh 10.80g (50mmol) of 4-nitrobenzyl bromide, dissolve it in 30mL (0.30mol) of ethyl acetate to form a solution, weigh 4.26g (50mmol) of N-methylpyrrolidine and dissolve it in 50mL (0.50mol) solution in ethyl acetate. Under the condition of stirring, the ethyl acetate solution of 4-nitrobenzyl bromide was slowly added dropwise into 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, washed 8 times with freshly distilled ethyl acetate, 20 mL each time, and then vacuum-dried to remove volatile components to obtain a light yellow solid powder. The obtained product was confirmed to be the compound described in the title by infrared spectrum and nuclear magnetic resonance spectrum analysis, and the yield was 95%. FTIR (cm -1 ): 3038, 3007, 2963, 2886, 1605, 1527, 1461, 13...

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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 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 the preparation method of the aforementioned pyrrolidinium ion compound. Background technique [0002] Ionic liquids refer to organic molten salts composed of specific relatively large-volume asymmetric organic cations and relatively small-volume inorganic or organic anions. Compared with traditional liquid substances (molecular solvents), ionic liquids are ionic compounds. Therefore, ionic liquids often exhibit unique properties and functions, and are a new class of "soft" functional materials or media with potential applications. [0003] When used as a solvent, compared to traditional solvents, ionic liquids have the following advantages: almost no vapor pressure, non-flammable, high thermal stability, and the physical and chemical prop...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/073C07D295/037C07D295/023C08G63/81
Inventor 刘正平窦军彦
Owner BEIJING NORMAL UNIVERSITY