Method for carrying out reductive amination reaction by adopting microchannel reaction device

A technology of microchannel reaction and microreactor, applied in chemical instruments and methods, preparation of organic compounds, preparation of amino compounds from amines, etc., can solve the problems of water and air sensitivity, release of borane and hydrogen, etc., and achieve toxicity And the effects of less pollution, short reaction time, and low production cost

Active Publication Date: 2021-12-17
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These reagents are also sensitive to water and air, and can release borane and hydrogen.

Method used

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  • Method for carrying out reductive amination reaction by adopting microchannel reaction device
  • Method for carrying out reductive amination reaction by adopting microchannel reaction device
  • Method for carrying out reductive amination reaction by adopting microchannel reaction device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the synthesis of compound 2a

[0036] Inject 1 mmol of benzyl alcohol (I), alcohol oxidase (~700 u), flavin adenine dinucleotide (FAD, 6 μmol, 5 mg), and hydrogen peroxide reductase (0.02 μmol, 4 mg) into syringe A. 10mL aqueous solution, suck air into syringe B, the flow rate of the two samples is 56.25μL min -1 After pumping into the micro-mixer 1 for mixing, then enter the micro-reactor 1 to react at 40°C for 25 minutes. Acetonitrile solution of aniline (1mmol, 0.1M) was injected into syringe C and mixed with the effluent from microreactor 1 through micromixer 2, then entered into microreactor 2 and reacted at 30°C for 8min. Add appropriate amount of water and ethyl acetate to the collected reaction solution for extraction, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain the crude product, which can be separated by column chromatography to obtain the target product 2a with a yield of 75%. NMR image such as figure 1...

Embodiment 2

[0037] Embodiment 2: the synthesis of compound 2b

[0038] Inject 1 mmol of benzyl alcohol (I), alcohol oxidase (~700 u), flavin adenine dinucleotide (FAD, 6 μmol, 5 mg), and hydrogen peroxide reductase (0.02 μmol, 4 mg) into syringe A. 10mL aqueous solution, suck air into syringe B, the flow rate of the two samples is 56.25μL min -1 After being mixed by the micro-mixer 1, enter the micro-reactor 1 to react at 40° C. for 25 min. Acetonitrile solution of 2-methylaniline (1mmol, 0.1M) was injected into syringe C and mixed with the effluent from microreactor 1 through micromixer 2, then entered into microreactor 2 and reacted at 30°C for 8min. Add appropriate amount of water and ethyl acetate to the collected reaction solution for extraction, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain the crude product, which can be separated by column chromatography to obtain the target product 2b with a yield of 76%.

Embodiment 3

[0039] Embodiment 3: the synthesis of compound 2c

[0040] Inject 1 mmol of benzyl alcohol (I), alcohol oxidase (~700 u), flavin adenine dinucleotide (FAD, 6 μmol, 5 mg), and hydrogen peroxide reductase (0.02 μmol, 4 mg) into syringe A. 10mL aqueous solution, suck air into syringe B, the flow rate of the two samples is 56.25μL min -1After being mixed by the micro-mixer 1, enter the micro-reactor 1 to react at 40° C. for 25 min. Acetonitrile solution of 3-chloroaniline (1mmol, 0.1M) was injected into syringe C and mixed with the effluent from microreactor 1 through micromixer 2, then entered into microreactor 2 and reacted at 30°C for 8min. Add appropriate amount of water and ethyl acetate to the collected reaction solution for extraction, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain the crude product, which can be separated by column chromatography to obtain the target product 2c with a yield of 71%.

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Abstract

The invention discloses a method for carrying out reductive amination reaction by adopting a microchannel reaction device. The microchannel reaction device comprises a microreactor 1 and a microreactor 2 which are connected in series, and the method comprises the following steps: (1) preparing a solution containing benzyl alcohol, alcohol oxidase, flavin adenine dinucleotide and hydrogen peroxide reductase as a first homogeneous solution, and preparing a solution of an aniline compound III as a second homogeneous solution; (2) mixing the first homogeneous solution with air, and simultaneously pumping a formed mixture into a microreactor 1 for reaction; and (3) mixing the reaction solution obtained in the step (2) with the second homogeneous solution, and simultaneously pumping a formed mixture into a microreactor 2 for reaction to obtain the N-benzylaniline compound as shown in a formula IV. The microreactor disclosed by the invention has the characteristics of high reaction safety, convenience in cleaning, easiness in amplification and the like. Meanwhile, compared with the prior art, the synthesis method has the advantages of simple, cheap and easily available initial materials, simple operation and high reaction efficiency, and is expected to be applied to industrial production.

Description

technical field [0001] The invention belongs to the technical field of reductive amination, in particular to a method for reductive amination reaction using a microchannel reaction device. Background technique [0002] Reductive amination reaction, also known as Bauch reduction, is a simple method to convert aldehydes and ketones into amines. Reductive amination plays an important role in organic synthesis, medicinal chemistry, biochemistry, etc. It is a key method to construct C-N bonds, and it is also one of the most useful and important tools for the synthesis of different kinds of amines. Currently, a large number of reductive amination methods have been reported corresponding to different types of substrates. In practical applications, there are two most common methods: The first method is to use platinum, palladium or nickel catalysts for catalytic hydrogenation. This is an economical method of reductive amination, especially in large-scale reactions. However, this ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/68C07C211/52C07C211/49C07C213/08C07C215/80B01J19/00
CPCC07C209/68C07C213/08B01J19/0093C07C211/52C07C211/49C07C215/80Y02P20/55
Inventor 乔凯石婷婷方正沈磊李玉光郭凯
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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