Compound containing cation radical of piperazidine, synthetic method, and application

A technology of cationic groups and compounds, applied in the field of compounds containing piperazine cationic groups and their synthesis and application, can solve problems such as simple synthetic routes

Inactive Publication Date: 2007-10-10
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Have not yet seen that the synthetic route is simple, the productive rate is h...

Method used

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  • Compound containing cation radical of piperazidine, synthetic method, and application
  • Compound containing cation radical of piperazidine, synthetic method, and application

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preparation example Construction

[0020] R in the above formula (1) 1, R 2 , R 3 and R 4 is butyl, X - The synthetic method that is the example compound of the present invention of fluoroborate anion comprises the following steps:

[0021] a. Add n-bromobutane to piperazine (the molar ratio of piperazine and n-bromobutane is 1:6), the solvent can be methanol, ethanol, propanol, isopropanol, N,N-dimethyl formamide, etc., heating reaction, the reaction temperature is 80°C, the pressure is 1-10 atmospheres, and the reaction time is 10-200 hours.

[0022] b, after the completion of the reaction (chromatographic detection), add ammonium fluoroborate (N, N, N', N'-tetrabutyl-piperazine ammonium bromide to ammonium fluoroborate molar ratio is 1: 2~ 6), the reaction temperature is 30°C, and the reaction time is 10-200 hours. The reaction product was purified to obtain N,N,N',N'-tetrabutylpiperazine ammonium fluoroborate.

[0023] same R 1 , R 2 , R 43 , R 4 for C 2 ~C 8 Alkyl, X is bromine or chloride ani...

Embodiment 1

[0026] N,N,N',N'-tetraethyl-piperazine ammonium bromide

[0027] Put 8.6 grams of piperazine, 100 grams of bromoethane and 150 grams of solvent methanol in the reaction device, the reaction temperature is 50 ° C, the pressure is 4 atmospheres, and the reaction time is 200 hours. After the reaction is completed (chromatographic detection), the solvent is evaporated . After the reaction product is purified, N,N,N',N'-tetrabutyl-piperazine ammonium bromide can be obtained, which is stable to air, and the yield is 93%.

[0028] m.p.: 50°C

[0029] High resolution mass spectrometry: [M-Br] + =200

[0030] 1 HNMR (D 2 O, δ / ppm relative to TMS): 3.625 (t, 8H), 3.281 (t, 8H), 1.251 (t, 12H).

Embodiment 2

[0032] N,N,N',N'-tetraisobutyl-piperazine ammonium chloride

[0033] Put 8.6 grams of piperazine, 180 grams of 2-chlorobutane and 150 grams of solvent ethanol in the reaction device, the reaction temperature is 80 ° C, the pressure is 1 atmosphere, and the reaction time is 100 hours. After the reaction (chromatographic detection), steam To solvent. The reaction product can be purified to obtain N,N,N',N'-tetrabutyl-piperazine ammonium chloride, which is air-stable, and the yield is 94%.

[0034] m.p.: 56°C

[0035] High resolution mass spectrometry: [M-Cl] + =312

[0036] 1 HNMR (D 2 O, δ / ppm relative to TMS): 3.332 (m, 4H), 3.615-3.618 (s, 8H), 1.714 (m, 8H), 1.332 (t, 12H), 0.964 (t, 12H).

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Abstract

This invention relates to a method for synthesizing a compound containing piperazine cation group and its application. The structural formula of the compound is shown, wherein, R1, R2, R3 and R4 are C1-C8 alkyl, and X- is Br-, Cl-, BF4- or PH6-. The compound has excellent properties of ionic liquid, and can dissolve a variety of poorly soluble compounds. The method has such advantages as low cost, simple synthesis, and high yield, and is suitable for mass production. The compound as ionic liquid can be used as gas absorbent and liquid extraction phase in separation engineering, reaction medium and catalyst in chemical reactions, electrolyte (including ion-conducting polyelectrolyte) in electrochemistry, cellulose solvent, multifunctional lubricant, matrix for mass spectrometry, and chromatographic stationary phase.

Description

technical field [0001] The invention relates to a compound containing piperazine cationic groups, a synthesis method and application thereof, and belongs to the technical field of organic chemical reaction methods. Background technique [0002] Ionic liquids (ionic liquids) are also called room temperature ionic liquids (room temperature ionic liquids), room temperature molten salts (room temperature molten salts), organic ionic liquids, etc., referred to as RTILs. for liquid salt. There are only anions and cations in ionic liquids, and there are no neutral molecules. Its main feature is that the cations are large and asymmetric, and the anions are small. According to the cations, the currently researched ionic liquids can be divided into: alkyl quaternary ammonium ions; alkyl quaternary phosphorus ions; 1,3-dialkyl substituted imidazolium ions; N-alkyl substituted pyridinium ions. According to anion, it can be divided into: metals (such as: AlCl 4 - 、CuC 2 - etc.) and...

Claims

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Application Information

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IPC IPC(8): C07D295/037
CPCC10N2220/04C10N2020/077
Inventor 周晓海张海波
Owner WUHAN UNIV
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