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Method for synthesizing amine compound catalyzed by functionalized ionic liquid

A technology of ionic liquids and compounds, which is applied in the field of synthesis of amine compounds, can solve the problems of high price and unfriendly environment, and achieve the effects of simple operation, simple post-treatment and good catalyst stability

Active Publication Date: 2013-05-01
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the above catalytic systems involve transition metals, noble metals or strong protonic acids, which are relatively expensive and environmentally unfriendly

Method used

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  • Method for synthesizing amine compound catalyzed by functionalized ionic liquid
  • Method for synthesizing amine compound catalyzed by functionalized ionic liquid
  • Method for synthesizing amine compound catalyzed by functionalized ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] At 80°C, p-toluenesulfonamide (0.75mmol, 128.3mg) and diphenylmethanol (0.5mmol, 92.0mg) and [BsTdmim]OTf (20mol%, 55.0mg), 1,4-dioxane 2.0mL was placed in a dry reaction bottle, and stirred by magnetic force for 3h. After the reaction was completed, column chromatography separated (using a silica gel column, eluent: petroleum ether / ethyl acetate=5 / 1) to obtain 154.9 mg of white solid N-benzhydryl-4-methylbenzenesulfonamide, producing The rate is 91.9%. 1 H NMR (400MHz, CDCl 3 )δ=2.37(s, 3H), 5.15(d, J=6.8Hz, 1H), 5.56(d, J=6.8Hz, 1H), 7.09-7.21(m, 12H), 7.56(d, J=8.0 Hz, 2H). 13 C NMR (100MHz, CDCl 3)δ=21.5, 61.4, 127.2, 127.4, 127.6, 128.5, 129.4, 137.3, 140.5, 143.2. HRMS-ESI: Calcd. For C 20 h 19 NNaO 2 S[M+Na] + :360.1029.Found: 360.1020.

Embodiment 2

[0036] With example 1, used catalyst is [TG][OTf], the productive rate of N-benzhydryl-4-methylbenzenesulfonamide is 79.3%.

Embodiment 3

[0038] With example 1, used catalyst is [LPS][OTf], the productive rate of N-benzhydryl-4-methylbenzenesulfonamide is 61.7%.

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Abstract

The invention discloses a method for synthesizing an amine compound catalyzed by functionalized ionic liquid. According to the method, functionalized ionic liquid is used as a catalyst to catalyze N-alkylation of amine and alcohol to synthesize corresponding compound derivatives. Acid functionalized ionic liquid is used as the catalyst to synthesize a series of compounds of amine. The method has the following advantages: a catalytic system is a metal-free system; the usage amount of the catalyst is small, and the catalyst has high catalytic activity, good stability and low corrosivity; operation is simple, and reaction is mild; post-treatment is easy, and the catalyst can be cyclically used.

Description

technical field [0001] The invention belongs to the field of synthesis of amine compounds, and in particular relates to a N-alkylation reaction between amines (including amides, sulfonamides, anilines and carbamates) and alcohols using functionalized ionic liquids as catalysts , a method for the synthesis of derivatives of the corresponding compounds. Background technique [0002] N-alkylation reaction is an important method for the synthesis of organic amines and their derivatives. Organic amines and their derivatives are important organic intermediate fragments and have important uses in organic synthesis, pharmaceuticals, polymer materials and fine product chemistry. Among them, sulfonamide derivatives are important drug intermediates, which can not be ignored in terms of sterilization, anti-inflammation, anti-virus, diuresis, anti-epileptic, lowering blood pressure, lowering blood sugar, lowering blood fat and inhibiting HIV protease. The traditional synthesis method o...

Claims

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Application Information

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IPC IPC(8): C07B43/04C07C303/40C07C311/16C07D263/22C07C311/03C07D257/04C07C209/18C07C211/52C07C231/12C07C233/65C07C269/06C07C271/12C07D231/12C07D213/81C07D223/10C07C233/09C07C233/05C07D249/08C07D207/267C07C233/03
Inventor 夏春谷韩峰杨磊李臻
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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