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Green Synthesis of Amino Alcohols Catalyzed by Visible Light

A green synthesis technology of amino alcohols, which is applied in the preparation of amino hydroxyl compounds, the preparation of organic compounds, organic chemical methods, etc., can solve the problems of complex experimental steps and low atom economy, and achieve simple synthetic routes and reliable reaction conditions. Good controllability and low cost effect

Active Publication Date: 2022-06-21
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • 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 of Amino Alcohols Catalyzed by Visible Light
  • Green Synthesis of Amino Alcohols Catalyzed by Visible Light
  • Green Synthesis of Amino Alcohols Catalyzed by Visible Light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] In a dry 10ml Schlenk tube, 90.4mg N-phenylglycine, 1.9mg photocatalyst [Ir(ppy) 2 dtbbpy]PF 6 , 2 ml of water, 20.4 μl of benzaldehyde, and the amount of benzaldehyde: N-phenylglycine: photocatalyst is 1:3:0.01. The reaction flask 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 455 nm blue light (Blue LED lamp) and stirred for 4 h. The distance between the Blue LED lamp and the Schlenk tube was 3 cm. After the reaction was detected by TLC, it was extracted 4 times with 5 ml 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 obtained residue is purified by column chromatography (PE / EA=5:1), as Figure 1-3 As shown, the synthesized product was indeed N-phenylphenethanolamine by qualitative and quantita...

Embodiment 2

[0080] In a dry 10ml Schlenk tube, 90.4mg N-phenylglycine, 1.9mg photocatalyst [Ir(ppy) 2 dtbbpy]PF 6 , 2 ml of water, 24.0 μl of p-methoxybenzaldehyde, and the ratio of the amount of p-methoxybenzaldehyde: N-phenylglycine: photocatalyst is 1:3:0.01. The reaction flask 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 455 nm blue light (Blue LED lamp) and stirred for 5 h. The distance between the Blue LED lamp and the Schlenk tube was 3 cm. After the reaction was detected by TLC, it was extracted 4 times with 5 ml 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 obtained residue is purified by column chromatography (PE / EA=4:1), as Figure 4-6 As shown, the synthesized product by qualitative and quantitative ...

Embodiment 3

[0082] In a dry 10ml Schlenk tube, 90.4mg N-phenylglycine, 1.9mg photocatalyst [Ir(ppy) 2 dtbbpy]PF 6 , 2 ml of water, 22.8 μl of p-toluidine, and the ratio of p-tolualdehyde:N-phenylglycine:photocatalyst is 1:3:0.01. The reaction flask was pumped and ventilated three times to ensure that there was no water and oxygen in the reaction tube, and then the reaction tube was sealed, and the reaction was placed under the irradiation of 455 nm blue light (Blue LED lamp) and stirred for 2 h. After the reaction was detected by TLC, it was extracted 4 times with 5 ml 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 obtained residue is purified by column chromatography (PE / EA=4:1), as Figure 7-9As shown, the synthesized product by qualitative and quantitative analysis is indeed 1-(p-methylphenyl)-2-(phenylamino)-ethan-1-ol, and the product...

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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. It specifically includes the following steps: S1. Add 90.4mg N-phenylglycine, 1.9mg photocatalyst, 2ml water, and 20.4ul benzaldehyde to a dry 10ml Schlenk tube sequentially; S2. Perform three gas exchange operations on the reaction bottle to ensure Seal the reaction tube after it is free of water and oxygen; S3, place the reaction under the irradiation of Blue LED and stir until the reaction is detected by TLC; S4, extract 4 times with 5ml of ethyl acetate, collect the organic phase, and wash 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 to obtain the product aminoalcohol compound. Compared with the prior art, the method has the characteristics of simple synthetic route, convenient operation, less environmental pollution, mild reaction conditions, good controllability of reaction conditions, wide application range of substrates and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a green synthesis method of amino alcohol compounds under visible light catalysis. Background technique [0002] Amino alcohol compounds, the chemical formula is: Among them, the β-amino alcohol compound contains both amino group and alcohol group, showing dual chemical reactivity of amine and alcohol, so it is widely used in various fields of production and life, such as: used as 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, anti-multidrug resistance marine natural products and so on. Therefore, the synthesis of amino alcohols has received extensiv...

Claims

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Application Information

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Patent Type & Authority Patents(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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