Preparation method of 3-hydroxy piperidine

A technology of hydroxypiperidine and hydroxypyridine, which is applied in the field of synthesis of 3-hydroxypiperidine, can solve the problems of long synthesis steps, poor atom economy, harsh reaction conditions, etc., achieve stable yield, weaken passivation, and recycle high rate effect

Inactive Publication Date: 2016-03-02
YUNNAN MINZU UNIV
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  • Abstract
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Problems solved by technology

[0008] In order to overcome the disadvantages of long synthesis steps of the above-mentioned prior art route, poor atom economy, harsh reaction conditions, etc., the present invention provides a new method for the synthesis of 3-hydroxypiperidine: using 3-hydroxypyridine as raw material, using rhodium-nickel / carbon As a bimetallic catalyst, phosphoric acid is used as an additive, and hydrogen is introduced into the reaction device to prepare 3-hydroxypiperidine at room temperature and lower reaction pressure

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  • Preparation method of 3-hydroxy piperidine
  • Preparation method of 3-hydroxy piperidine
  • Preparation method of 3-hydroxy piperidine

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Experimental program
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Effect test

Embodiment 1

[0025] Weigh 1 g of rhodium-nickel / carbon bimetallic catalyst (10% rhodium and 1% nickel), 10 g (0.11 mol) of 3-hydroxypyridine, 0.3 g (3.1 mmol) of phosphoric acid, and isopropanol (55 mL) As a solvent, put it into the reactor and pass hydrogen to the internal pressure of 3atm, 25 o C reacted for 3h, released hydrogen after the reaction was over, filtered the catalyst, concentrated the reaction solution under reduced pressure, and obtained crude product was distilled under reduced pressure (65-67 oC ,2mmHg) to get 10.7g of 3-hydroxypiperidine, yield: 96%; 1 HNMR (400MHz, CDCl 3 ):δ=3.56(m,1H),2.99(m,1H),2.80-2.39(m,3H),1.93(m,1H),1.74(m,1H),1.51-1.33(m,3H)ppm .

Embodiment 2

[0027] Weigh 500g of rhodium-nickel / carbon bimetallic catalyst (the rhodium content is 5%, the nickel content is 0.5%), 3-hydroxypyridine 10kg (105.3mol), phosphoric acid 0.5kg (5.1mol), water (42L) as solvent , put into the reactor and pass hydrogen to the internal pressure of 5atm, 50 o C reacted for 30min, released hydrogen after the reaction was over, filtered the catalyst, and the reaction liquid was distilled under reduced pressure (65-67 o C, 2mmHg) to obtain 9.78kg of 3-hydroxypiperidine, yield: 92%.

Embodiment 3

[0028] Embodiment 3 Catalyst recovery experiment

[0029] Weigh 100g of rhodium-nickel / carbon bimetallic catalyst (wherein rhodium content is 10%, nickel content is 1%), 3-hydroxypyridine 1kg (10.53mol), phosphoric acid 30g (0.31mol), water (5L) as solvent, Put hydrogen into the reactor to the internal pressure of 3atm, 50 o C reaction, release hydrogen after the reaction is over, filter out the catalyst and directly use it for the next catalytic cycle, and the reaction liquid is distilled under reduced pressure (65-67 oC , 2mmHg) to 3-hydroxypiperidine. Catalyst recycling 8 times product yield is as follows:

[0030] Cycles Reaction time (h) Product yield (%) 1 1 95 2 1 94.5 3 1 93.8 4 1.5 94.5 5 1.5 93.2 6 2 94 7 2 94.5 8 2 94

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Abstract

The invention discloses a preparation method of 3-hydroxy piperidine. The method comprises: subjecting 3-hydroxy pyridine and rhodium-nickel/carbon bi-metal hydrogenation catalyst to reduction reaction in water or an organic solvent under a hydrogen atmosphere so as to obtain 3-hydroxy piperidine. Compared with the existing synthesis method, the method adds the metal additive nickel to improve the hydrogenation catalytic activity of rhodium carbon, carries out reduction reaction under mild conditions, and reduces the equipment pressure. In addition, the rhodium-nickel/carbon bi-metal catalyst has high activity of reducing 3-hydroxy pyridine, has stable properties, and can achieve a product yield of greater than 90%, thus creating good conditions for large-scale production of 3-hydroxy piperidine.

Description

technical field [0001] The invention relates to a synthesis method of 3-hydroxypiperidine. Background technique [0002] 3-Hydroxypiperidine alkaloids are a class of alkaloids containing piperidine rings that widely exist in nature, and most of them have physiological activities. For example, swainsonine isolated from fungi and Australian plants Swainsonine anescens can inhibit malignant tumor cells N - Synthesis of linked oligosaccharides, which have anti-cancer and immune-enhancing effects; Changshanine, which is isolated from the traditional Chinese medicine Changshan, has significant antimalarial activity. In addition, 3-hydroxypiperidine is also a key structural unit of many drugs and candidate drugs, and 3-hydroxypiperidine exists in antiarrhythmic drugs, calcium antagonists, oxygen squalene cyclase inhibitors, and serotonin receptor agonists. Piperidine fragments. [0003] In recent years, the market demand for 3-hydroxypiperidine as a pharmaceutical intermediate ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/42
CPCC07D211/42
Inventor 蒋琳袁明龙袁明伟李宏利钏永明袁明虎彭金辉
Owner YUNNAN MINZU UNIV
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