Method for preparing fluorine-containing secondary amine
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A technology for fluorine-containing secondary amines and primary amines, applied in the field of preparation of fluorine-containing secondary amines, to achieve the effects of easy access, low toxicity, high atom economy and step economy
Inactive Publication Date: 2017-05-31
NANJING UNIV OF SCI & TECH
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However, most of the current studies focus on substrates such as alkyl alcoh
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Embodiment 1
[0020]
[0021] Under nitrogen protection, sequentially add [Cp*IrCl 2 ] 2 0.006mmol, aniline 0.3mmol, fluoroethanol 0.33mmol, sodium bicarbonate 0.006mmol and toluene 0.5mL, heated to 100°C and reacted for 24h. After the reaction, cool down to room temperature, add a small amount of water, extract three times with 15 mL of ethyl acetate, combine the organic phases, then wash with saturated brine, dry over anhydrous magnesium sulfate, evaporate the solvent under reduced pressure, and separate the secondary amine by column chromatography. 76%
Embodiment 2
[0023]
[0024] Under nitrogen protection, sequentially add [Cp*IrCl 2 ] 2 0.006mmol, 0.3mmol of aniline, 0.33mmol of fluoroethanol, 0.03mmol of triethylamine and 0.5mL of toluene, heated to 100°C and reacted for 24h. After the reaction, cool down to room temperature, add a small amount of water, extract three times with 15 mL of ethyl acetate, combine the organic phases, then wash with saturated brine, dry over anhydrous magnesium sulfate, evaporate the solvent under reduced pressure, and separate the secondary amine by column chromatography. 75%.
Embodiment 3
[0026]
[0027] Under nitrogen protection, sequentially add [Cp*IrCl 2 ] 2 0.006mmol, aniline 0.3mmol, fluoroethanol 0.33mmol, sodium bicarbonate 0.006mmol and dioxane 0.5mL, heated to 100°C and reacted for 24h. After the reaction, cool down to room temperature, add a small amount of water, extract three times with 15 mL of ethyl acetate, combine the organic phases, then wash with saturated brine, dry over anhydrous magnesium sulfate, evaporate the solvent under reduced pressure, and separate the secondary amine by column chromatography. 75%.
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Abstract
The invention discloses a synthetic method of a fluorine-containing secondary amine compound. Pentamethylcyclopentadienyl iridium chloride dimer is used as a metal catalyst, fluoroalkyl comes from fluorinated alcohol, alkali is used as a co-catalyst, and the fluorine-containing secondary amine is prepared via the following step: primary amine reacts with the fluorinated alcohol under the action of the transition metal iridium catalyst and the alkali in an organic solvent to obtain the fluorine-containing secondary amine compound. The method overcomes the defects in the prior art that the fluorine-containing alkylating agent is high in toxicity and instable and needs to be prepared in advance, the reaction operation is complex, the steps are fussy and the like, and can obtain considerable yield. The adopted fluorinated alcohol is readily available, stable in chemical property and low in toxicity. The method is simple in reaction, has very high atom economy and step economy, and is energy-saving, environment-friendly and simple in operation. By adopting [Cp*IrCl2]2 as the catalyst, ligands are not needed, and the system is easy to realize.
Description
technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing fluorine-containing secondary amines. Background technique [0002] Secondary amine is a very important structural unit, which widely exists in medicine, pesticide and natural product molecules. Alkylation of primary amines is a basic but important method for the preparation of secondary amines. Since the middle of the 20th century, the importance of fluorine-containing compounds has become more and more prominent in various fields, especially in the field of life sciences. According to statistics, more than 20% of approved drugs and 30-40% of commercialized pesticides contain fluorine. We imagine that if fluorine-containing alkyl chains are introduced into primary amines, the prepared fluorine-containing secondary amines may have some special pharmaceutical activities. Therefore, the research on the preparation of fluorine-containing seconda...
Claims
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