Green synthesis method of amino alcohol compounds under visible light catalysis

An amino alcohol, green synthesis technology, applied in the preparation of amino hydroxy compounds, the preparation of organic compounds, organic chemical methods and other directions, can solve the problems of complex experimental steps, low atom economy, etc., to achieve simple synthesis route and reaction conditions. Good controllability and high productivity

Active Publication Date: 2019-12-10
HANGZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has complicated experimental steps and low atom economy

Method used

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  • Green synthesis method of amino alcohol compounds under visible light catalysis
  • Green synthesis method of amino alcohol compounds under visible light catalysis
  • Green synthesis method of amino alcohol compounds under visible light catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] In a dry 10ml Schlenk tube, add 90.4mg N-phenylglycine, 1.9mg photocatalyst [Ir(ppy) 2 dtbbpy]PF 6 , 2ml of water, 20.4 μl of benzaldehyde, the ratio of benzaldehyde: N-phenylglycine: photocatalyst is 1:3:0.01. The reaction bottle was pumped and ventilated three times to ensure that the reaction tube was anhydrous and oxygen-free, then sealed, and the reaction was placed under the irradiation of 455nm blue light (Blue LED light) and stirred for 4 hours. The distance between the Blue LED light and the Schlenk tube was 3cm. After the reaction was detected by TLC, it was extracted 4 times with 5ml of ethyl acetate respectively, and the organic phase was collected and washed with anhydrous Na 2 SO 4 Drying, adding an appropriate amount of silica gel and concentrating under reduced pressure, and the resulting residue was purified by column chromatography (PE / EA=5:1), as Figure 1-3 As shown, the synthesized product was indeed N-phenylphenylethanolamine through qualitative...

Embodiment 2

[0080] In a dry 10ml Schlenk tube, add 90.4mg N-phenylglycine, 1.9mg photocatalyst [Ir(ppy) 2 dtbbpy]PF 6 , 2ml of water, 24.0 μl of p-methoxybenzaldehyde, p-methoxybenzaldehyde: N-phenylglycine: photocatalyst in a ratio of 1:3:0.01. The reaction bottle was pumped and ventilated three times to ensure that the reaction tube was anhydrous and oxygen-free, then sealed, and the reaction was placed under 455nm blue light (Blue LED light) and stirred for 5 hours. The distance between the Blue LED light and the Schlenk tube was 3cm. After the reaction was detected by TLC, it was extracted 4 times with 5ml of ethyl acetate respectively, and the organic phase was collected and washed with anhydrous Na 2 SO 4 Dry, add an appropriate amount of silica gel and concentrate under reduced pressure, and the resulting residue is purified by column chromatography (PE / EA=4:1), as Figure 4-6 Shown, the synthetic product by qualitative and quantitative analysis is indeed 1-(4-methoxyphenyl)-2-(...

Embodiment 3

[0082] In a dry 10ml Schlenk tube, add 90.4mg N-phenylglycine, 1.9mg photocatalyst [Ir(ppy) 2 dtbbpy]PF 6 , 2ml of water, 22.8 μl of p-tolualdehyde, the ratio of p-tolualdehyde: N-phenylglycine: photocatalyst is 1:3:0.01. The reaction bottle was pumped and ventilated three times to ensure that there was no water and oxygen in the reaction tube, and then sealed, and the reaction was placed under the irradiation of 455nm blue light (Blue LED lamp) and stirred for 2h. After the reaction was detected by TLC, it was extracted 4 times with 5ml of ethyl acetate respectively, and the organic phase was collected and washed with anhydrous Na 2 SO 4 Dry, add an appropriate amount of silica gel and concentrate under reduced pressure, and the resulting residue is purified by column chromatography (PE / EA=4:1), as Figure 7-9Shown, the synthetic product by qualitative and quantitative analysis is indeed 1-(p-methylphenyl)-2-(phenylamino)-ethan-1-alcohol, obtains product 1-(p-methylphenyl)...

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Abstract

The invention discloses a green synthesis method of amino alcohol compounds under visible light catalysis, and belongs to the technical field of organic synthesis. The green synthesis method specifically comprises the following steps that S1, 90.4mg of N-phenylglycine, 1.9mg of a photocatalyst, 2ml of water and 20.4ul of benzaldehyde are added in sequence into 10ml of a dried Schlenk tube; S2, three times of air extraction operation is conducted on a reaction bottle to ensure that no water or oxygen exists in a reaction tube before sealing; S3, the reaction bottle is placed under Blue LED irradiation, mixing is conducted until TLC detecting reaction is finished; and S4, 5 ml of ethyl acetate is correspondingly extracted for 4 times, organic phases are collected, anhydrous Na2SO4 is used for drying, appropriate silica gel is added and concentrated under decompression, and obtained residues are purified through column chromatography to obtain the product amino alcohol compounds. Comparedwith the prior art, the green synthesis method has the characteristics of simple synthesis route, easy and convenient operation, little environmental pollution, mild reaction conditions, good controllability of reaction conditions, and wide application range of substrates.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a green synthesis method of amino alcohol compounds under visible light catalysis. Background technique [0002] Amino alcohol compound, the chemical formula is: Among them, the β-amino alcohol compound contains both amino and alcohol groups, showing the dual chemical reactivity of amine and alcohol, so it is widely used in various fields of production and life, such as: as a polymer material catalyst, pigment dispersant, industrial Fluid emulsifiers and formaldehyde fixatives, organic synthesis reagents (especially the synthesis of small molecule drugs), etc. In addition, the structure of amino alcohols is also widely found in many biologically active natural products, such as anti-AIDS drugs, anti-hypertensive drugs, cordyceps sinensis myriocin, anti-multidrug resistance marine natural products and so on. Therefore, the synthesis of aminoalcohols has re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B61/00C07C213/00C07C215/30C07C217/70C07C215/16C07D307/52C07D333/20C07D207/08
CPCC07B61/02C07C213/00C07D307/52C07D333/20C07D207/08C07C215/30C07C217/70C07C215/16
Inventor 曾晓飞钟国富潘舒蕾
Owner HANGZHOU NORMAL UNIVERSITY
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