Novel method for preparing secondary amine by reaction of primary amine and tertiary amine
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A technology for tertiary amines and secondary amines, applied in chemical instruments and methods, formation/introduction of amino groups, preparation of organic compounds, etc., can solve problems such as difficult demethylation of N-methylamine
Active Publication Date: 2015-06-17
JIANGNAN UNIV
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Problems solved by technology
However, it is not easy to achieve efficient and selective demethylation of N-methylamines in chemical reactions
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Embodiment 1
[0021] Embodiment one: a kind of novel method that obtains secondary amine by reaction of aniline and triethylamine comprises the following process steps:
[0022] Under nitrogen protection, in 50mL Schlenk tube, add aniline (93mg, 1mmol), triethylamine (304mg, 3mmol), [(Bt) 2 *Ir*P(nBu) 3 ]OTf (9.6mg, 0.01mmol, 1.0mol%), add 2.0mL xylene; react the reaction solution at 155°C for 10h, and separate the resulting solution with a 200-300 mesh silica gel column (the eluent is 1:10 ethyl acetate ester / petroleum ether), and the product was obtained after removing the solvent.
[0023] Yield: 95%.
Embodiment 2
[0024] Embodiment two: a kind of novel method that obtains secondary amine by reacting 4-methoxyaniline and triethylamine, comprises the following processing steps:
[0025] Under nitrogen protection, in 50mL Schlenk tube, add 4-methoxyaniline (123mg, 1mmol), triethylamine (304mg, 3mmol), [(Bt) 2 *Ir*P(nBu) 3 ]OTf (9.6mg, 0.01mmol, 1.0mol%), add 2.0mL xylene; react the reaction solution at 155°C for 10h, and separate the resulting solution with a 200-300 mesh silica gel column (the eluent is 1:10 ethyl acetate ester / petroleum ether), and the product was obtained after removing the solvent.
[0026] Yield: 92%.
Embodiment 3
[0027] Embodiment three: a kind of novel method that obtains secondary amine by reacting 4-methylaniline and triethylamine, comprises the following processing steps:
[0028] Under nitrogen protection, in 50mL Schlenk tube, add 4-methylaniline (107mg, 1mmol), triethylamine (304mg, 3mmol), [(Bt) 2 *Ir*P(nBu) 3 ]OTf (9.6mg, 0.01mmol, 1.0mol%), add 2.0mL xylene; react the reaction solution at 155°C for 10h, and separate the resulting solution with a 200-300 mesh silica gel column (the eluent is 1:10 ethyl acetate ester / petroleum ether), and the product was obtained after removing the solvent.
[0029] Yield: 96%.
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Abstract
The invention discloses a novel method for preparing secondary amine by a reaction of primary amine and tertiary amine. The method comprises the following steps of 1, adding primary amine and tertiary amine into a reaction container according to a mole ratio of primary amine to tertiary amine of 1: 3, adding [(Bt)2*Ir*P(nBu)3]OTf as a catalyst (wherein Bt represents phenylbenzothiazole) into the reaction container, adding an organic solvent into the reaction container, and carrying out a reaction process at a temperature of 120-160 DEG C for 6-12h, wherein a mole ratio of primary amine, tertiary amine to catalyst is 1: 3: 0.01, and 2, carrying out purification by a silica gel column of 200-300 meshes, pre-leaching the silica gel column by 20-50mL of petroleum ether, carrying out elution on the leacheate at a leacheate flowing rate of 1-2mL / min for 3-6h so that the solvent is removed and the corresponding secondary amine product is obtained. A research result shows that the novel method for producing secondary amine by a reaction of primary amine and tertiary amine has the characteristics of mild conditions, high conversion rate and no pollutant. The method solves the problems of the existing secondary amine synthesis method and improves secondary amine synthesis.
Description
technical field [0001] The invention relates to a new method for obtaining a secondary amine through the reaction of a primary amine and a tertiary amine, and belongs to the field of chemical materials and medicines. Background technique [0002] With the increasingly prominent environmental problems, more attention has been paid to green chemistry, and the development of environmentally friendly catalytic systems and synthetic methods has attracted more and more attention of organic chemists. [0003] Secondary amines are an important class of chemicals, mainly used as dyes, spices and pesticides, pharmaceutical synthesis intermediates, rubber antioxidants and stabilizers for fibers, plastics and rubber. In recent years, as the use of secondary amines has been extensively explored, the synthesis of secondary amines has become increasingly important. Traditional secondary amines are mostly prepared by reacting amines with halogenated hydrocarbons, alkylsulfonate dioxane fro...
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