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Method for preparing 1,4-dihydropyridine compounds by utilizing micro-reaction device

A technology of micro-reaction device and dihydropyridine, which is applied in the direction of organic chemistry, can solve the problems of difficult separation of homogeneous catalysts, low degree of automation, active site blocking, etc., and achieve short reaction residence time, high safety, and easy The effect of operational control

Active Publication Date: 2018-01-09
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Purpose of the invention: In order to solve the difficulty in the separation of homogeneous catalysts used in the preparation of 1,4-dihydropyridine compounds, the blockage of active sites of heterogeneous catalysts, the degradation of catalysts under acidic conditions, and the low degree of automation and low yield of batch preparation and the problem of many side reactions, the invention provides a method for preparing 1,4-dihydropyridine compounds using a micro-reaction device

Method used

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  • Method for preparing 1,4-dihydropyridine compounds by utilizing micro-reaction device

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Embodiment 1

[0026] Dissolve benzaldehyde, ethyl acetoacetate and ammonium acetate into a homogeneous phase (wherein the molar ratio of benzaldehyde: ethyl acetoacetate: ammonium acetate = 1:2:1.5) is recorded as solution A, and the particle size is 10nm γ- Fe 2 o 3 Nanoparticles dispersed in absolute ethanol (where γ-Fe 2 o 3 The concentration of nanoparticle is 250mg / mL) is recorded as solution B; Then solution A and solution B are mixed through micro-mixer, wherein solution A adopts HPLC pump to inject in the micro-mixer, and solution B adopts slurry pump to inject in the micro-mixer, γ-Fe 2 o 3 The molar ratio of nanoparticles to aromatic aldehyde was 0.05:1, mixed well and injected into the microreactor (the inner diameter of the capillary of the microreactor was 1mm, and the capillary volume was 5mL) and reacted at 120°C for 5min. The output of the microreactor is centrifuged to obtain an organic phase, and the organic phase is washed with Na 2 CO 3 After alkali washing and di...

Embodiment 2

[0029] Dissolve benzaldehyde, ethyl acetoacetate and ammonium acetate into a homogeneous phase (the molar ratio of benzaldehyde: ethyl acetoacetate: ammonium acetate is 1:3:2) and record it as solution A, the particle size is 10nm gamma-Fe 2 o 3 Nanoparticles dispersed in absolute ethanol (where γ-Fe 2 o 3The concentration of nanoparticles is 350 mg / mL) as solution B; then solution A and solution B are mixed through a micro-mixer, wherein solution A is injected into the micro-mixer using an HPLC pump, and solution B is injected into the micro-mixer using a slurry pump , γ-Fe 2 o 3 The molar ratio of nanoparticles to aromatic aldehyde was 0.1:1, mixed well and injected into the microreactor (the inner diameter of the capillary of the microreactor was 1mm, and the capillary volume was 7mL) and reacted at 130°C for 7.5min. The output of the microreactor is centrifuged to obtain an organic phase, and the organic phase is washed with Na 2 CO 3 After alkali washing and distill...

Embodiment 3

[0032] Dissolve benzaldehyde, ethyl acetoacetate and ammonium acetate into a homogeneous phase (wherein the molar ratio of benzaldehyde: ethyl acetoacetate: ammonium acetate is 1:4:3) is recorded as solution A, and the particle size is 50nm gamma-Fe 2 o 3 Nanoparticles dispersed in absolute ethanol (where γ-Fe 2 o 3 The concentration of nanoparticles is 450 mg / mL) as solution B; then solution A and solution B are mixed through a micro-mixer, wherein solution A is injected into the micro-mixer using an HPLC pump, and solution B is injected into the micro-mixer using a slurry pump , γ-Fe 2 o 3 The molar ratio of nanoparticles to aromatic aldehyde was 0.15:1, mixed well and poured into the microreactor (the inner diameter of the capillary of the microreactor was 1mm, the capillary volume was 9mL) and reacted at 140°C for 10min. The output of the microreactor is centrifuged to obtain an organic phase, and the organic phase is washed with Na 2 CO 3 After alkali washing and di...

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Abstract

The invention discloses a method for preparing 1,4-dihydropyridine compounds by utilizing a micro-reaction device. The method comprises the following steps: mixing and dissolving aromatic aldehyde compounds, beta-dicarbonyl compounds and an ammonium salt so as to obtain a solution A; dispersing gamma-Fe2O3 nano-particles into absolute ethyl alcohol to obtain a solution B; respectively and simultaneously pumping the solution A and the solution B into a micro-mixer in the micro-reaction device, fully mixing, and introducing into the micro-reactor in the micro-reaction device to be reacted; centrifuging the discharged material in the micro-reactor to obtain an organic phase, washing the organic phase, performing vacuum concentration to obtain a coarse product, and separating and purifying thecoarse product, thereby obtaining the product. The highest yield of the 1,4-dihydropyridine compounds prepared by the invention can reach 99.9%, and the reason that the gamma-Fe2O3 nano-particles canbe repeatedly used by 30 times and the yield is invariable is because high catalytic activity can be always maintained when the product and toxins are continuously removed from the metal oxide surface. Moreover, any by-product is not produced in the method disclosed by the invention.

Description

technical field [0001] The invention relates to the preparation of compounds, in particular to a method for preparing 1,4-dihydropyridine compounds using a micro-reaction device. Background technique [0002] Since Hantzsch synthesized 1,4-dihydropyridine for the first time in 1882, researchers have found that this type of compound has a variety of biological activities, such as anti-mutation, anti-tumor, bronchial expansion and hypoglycemic. In addition, 1,4-dihydropyridine compounds are also used as calcium ion channel blockers, NADPH regeneration agents, reducing agents for transfer hydrogenation reactions, and organic synthesis intermediates. [0003] Considering the importance of 1,4-dihydropyridine to the study of synthetic chemistry and biological activity, researchers have conducted extensive and in-depth studies on the synthetic pathway of 1,4-dihydropyridine. The classic Hantzsch reaction (hanchpyridine synthesis reaction) includes Knoevenagel condensation and ene...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/82C07D211/90
Inventor 郭凯何伟方正朱宁李昕欧阳平凯
Owner NANJING TECH UNIV
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