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Novel synthesis process of N-benzyl-3-piperidinol, novel nickel-based catalyst and preparation method thereof

A nickel-based catalyst and synthesis process technology, applied in chemical instruments and methods, physical/chemical process catalysts, metal/metal oxide/metal hydroxide catalysts, etc., can solve the requirement of reducing hydrogen pressure and the high cost of precious metal catalysts , the cost is difficult to reduce and other problems, to achieve the effect of reducing pressure resistance requirements, significant economic and social benefits, and reducing production costs

Inactive Publication Date: 2012-12-19
ANHUI SHENGDONG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] This approach is the general technique of producing N-benzyl-3-piperidinol both at home and abroad at present, and the producer that uses is more, because it has taken noble metal catalysts such as platinum dioxide, platinum carbon, rhodium carbon, greatly reduces for Requirements for hydrogen pressure, usually the reaction can be completed below 5 atmospheres, the requirements for equipment are reduced, and the safety of operation is also improved; however, the cost of noble metal catalysts is very high, and the cost of the entire process route is still difficult to reduce

Method used

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  • Novel synthesis process of N-benzyl-3-piperidinol, novel nickel-based catalyst and preparation method thereof
  • Novel synthesis process of N-benzyl-3-piperidinol, novel nickel-based catalyst and preparation method thereof
  • Novel synthesis process of N-benzyl-3-piperidinol, novel nickel-based catalyst and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0047] Prepare the nickel-based catalyst as follows:

[0048] (1) 700g of diatomaceous earth is added into a three-necked round bottom flask with a capacity of 20L;

[0049] (2) 1250ml of 95% ethanol, 290g of nickel acetate, and 84.25g of cobalt chloride were also added to the aforementioned three-necked round-bottomed flask, fully dissolved, and soaked overnight;

[0050] (3) Slowly add 80 g of sodium borohydride solution (0.2 mol / L) under vigorous stirring, and fully react until no bubbles are released;

[0051] (4) After completion of the reaction, add 4L of water and filter with suction to obtain about 850g of the nickel-based catalyst (wherein the active ingredient is about 150g);

[0052] (5) Wash the nickel-based catalyst for 3 to 5 times, wash each time with 1000 ml of water, drain and store in 95% ethanol for later use.

Embodiment 2

[0054] Prepare N-benzyl-3-piperidinol as follows:

[0055] (1) Add 95g of 3-hydroxypiperidine and 500mL of toluene into a three-neck round bottom bottle equipped with mechanical stirring, thermometer, and constant pressure dropping funnel, and heat to 90°C;

[0056] (2) After the 3-hydroxypyridine is completely dissolved in toluene, 130 g of benzyl chloride is slowly added dropwise therein, and the dropwise addition is completed within 30 minutes;

[0057] (3) Keep at 90°C and react for 2 hours;

[0058] (4) stop heating, continue to stir and cool to room temperature, separate out a large amount of white solids;

[0059] (5) filter the separated white solid to obtain the quaternary ammonium salt of N-benzyl-3-hydroxypyridine, and wash the filter cake once with toluene 200mL;

[0060] (6) Add the washed quaternary ammonium salt of N-benzyl-3-hydroxypyridine into the hydrogenation kettle, add 500 mL of absolute ethanol, 101 g of triethylamine, and 30 g of the nickel-based cata...

Embodiment 3

[0070] Prepare N-benzyl-3-piperidinol as follows:

[0071] (1) Add 1.9Kg of 3-hydroxypiperidine and 10L of toluene into a 20L enamel reaction kettle equipped with mechanical stirring, enamel disk condenser, thermometer and metering pump, and heat to 110°C;

[0072] (2) After the 3-hydroxypyridine is completely dissolved in toluene, 2.6Kg of benzyl chloride is slowly added dropwise therein, and the dropwise addition is completed within 30 minutes;

[0073] (3) Keep at 110°C and react for 2 hours;

[0074] (4) stop heating, continue to stir and cool to room temperature, separate out a large amount of white solids;

[0075] (5) filter the separated white solid to obtain the quaternary ammonium salt of N-benzyl-3-hydroxypyridine, and wash the filter cake once with 4L of toluene;

[0076] (6) Join the quaternary ammonium salt of the washed N-benzyl-3-hydroxypyridine in a 20L hydrogenation kettle, add 10L of dehydrated alcohol, 2.1Kg of triethylamine, and 600g of the nickel-based ...

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Abstract

The invention discloses a synthesis process of N-benzyl-3-piperidinol which is the most important midbody for synthesizing Benidipine. The synthesis process comprises the following steps of: taking 3-hydroxy pyridine as a raw material, firstly performing the reaction with benzyl chloride to generate quaternary ammonium salt of N-benzyl-3-hydroxy pyridine, then carrying out catalytic reduction on the quaternary ammonium salt under the moderate hydrogen pressure (3 to 5atm) by using a nickel-based catalyst which is low in cost and easy to be prepared so as to obtain the N-benzyl-3-piperidinol. The invention also discloses a formula and a preparation method of the nickel-based catalyst used in the synthesis process of the N-benzyl-3-piperidinol. The invention has the advantages of low cost, safe operation, high product purity, and the like and is a synthesis route of the N-benzyl-3-piperidinol which is environment-friendly and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of N-benzyl-3-piperidinol, in particular to a synthesis process of N-benzyl-3-piperidinol, a nickel-based catalyst and a preparation method. Background technique [0002] Since the 1980s, the incidence of hypertension in my country has continued to rise. According to the statistics of the health department, the number of hypertensive patients in my country has reached 1% of the total population. Accordingly, the market share of antihypertensive drugs has also increased sharply year by year. my country's antihypertensive drug market is basically dominated by three major categories of drugs: dipine, sartan and prix. Among them, the antihypertensive drugs of the dipine type are the most popular among patients, because of their cheap price and definite curative effect, they can be the most popular medicine for the vast number of middle-aged people in my country. accepted by low-income groups. [0003] Benidipin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/42C07D211/02B01J23/755
Inventor 刘前
Owner ANHUI SHENGDONG CHEM