Synthesizing method of 1-benzyl-piperidone hydrochloride

A technology of piperidone hydrochloride and synthesis method, which is applied in the field of synthesis of 1-benzyl-3-piperidone hydrochloride, and can solve the problems of reducing hydrogen pressure, difficult cost reduction, and high cost of precious metal catalysts , to achieve the effects of short steps, cost reduction and safe operation

Inactive Publication Date: 2012-02-15
兰州博实生化科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] This approach is the general technique of producing 1-benzyl-3-piperidone hydrochloride at home and abroad at present, and the producer that uses is more, because it has taken such as precious metal catalysts such as platinum dioxide, platinum carbon, rhodium carbon, greatly The requirement for

Method used

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  • Synthesizing method of 1-benzyl-piperidone hydrochloride
  • Synthesizing method of 1-benzyl-piperidone hydrochloride
  • Synthesizing method of 1-benzyl-piperidone hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0034] The synthetic method of 1-benzyl-3-piperidone hydrochloride comprises the steps:

[0035]

[0036] (1) Weigh 30 grams (0.32mol) of the raw material 3-hydroxypyridine, add 400ml of toluene, heat to dissolve, and under reflux, add 40 (0.32mol) benzyl chloride dropwise, finish adding within 30 minutes, and continue to reflux React for 2 hours. TLC detects that the reaction is complete. After the reaction was cooled to room temperature, it was suction filtered and dried to obtain 65 g of product A, with a yield of 94%.

[0037]

[0038] (2) Add 65 g (0.29 mol) of the product A prepared in the first step to 800 ml of ethanol, slowly add 22.33 (0.59 mol) of sodium borohydride in batches under ice bath, and return to room temperature and stir for 10-15 Hour. As detected by TLC, the reaction was complete, and 200 ml of water was added to quench the reaction solution. Spin off the ethanol, add concentrated hydrochloric acid to adjust the pH to 1-2, extract impurities t...

Embodiment 2

[0042] The synthetic method of 1-benzyl-3-piperidone hydrochloride comprises the steps:

[0043]

[0044] (1) Weigh 300 (3.2mol) grams of raw material 3-hydroxypyridine, add 5000ml of toluene, heat to dissolve, under reflux, add 390g (3.08mol) of benzyl chloride dropwise, finish adding within 60 minutes, and continue to reflux React for 2 hours. TLC detects that the reaction is complete. After the reaction was cooled to room temperature, it was suction filtered and dried to obtain 630 g of product A with a yield of 90%.

[0045]

[0046] (2) Add 630 g (2.85 mol) of the product A prepared in the first step to 8000 ml of ethanol, slowly add 250 (6.6 mol) grams of sodium borohydride in batches under ice bath, return to room temperature and stir for 10-15 Hour. TLC detects that the reaction is complete. Add 2000 ml of water to quench the reaction solution. Spin off the ethanol, add concentrated hydrochloric acid to adjust the pH to 1-2, extract impurities twice with 1000 ...

Embodiment 3

[0050] The synthetic method of 1-benzyl-3-piperidone hydrochloride comprises the steps:

[0051]

[0052] (1) Weigh 1000 g (10.52 mol) of raw material 3-hydroxypyridine, add 5000 ml of toluene, heat to dissolve, and add 1280 g (10.11 mol) of benzyl chloride dropwise under reflux, finish adding within 60 minutes, and continue to reflux React for 2 hours. TLC detects that the reaction is complete. After the reaction was cooled to room temperature, it was suction filtered and dried to obtain 2165 g of product A with a yield of 93%.

[0053]

[0054] (2) Add 2165 g (9.79 mol) of the product A prepared in the first step to 15 liters of ethanol, slowly add 800 g (21.12 mol) of sodium borohydride in batches under ice bath, and return to room temperature and stir for 10-15 Hour. TLC detects that the reaction is complete. Add 2000 ml of water to quench the reaction solution. Spin off the ethanol, add concentrated hydrochloric acid to adjust the pH to 1-2, extract the impurit...

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Abstract

The invention discloses a synthesizing method of 1-benzyl-piperidone hydrochloride. The method comprises steps that: (1) 3-hydroxypyridine is added to an organic solvent, and is refluxed under a temperature of 100 to 110 DEG C; benzyl halide is dropped into the solution, and the refluxing reaction is continued for 2 to 4 hours, such that a product A is obtained; (2) the product A is added to an alcohol organic solvent; sodium borohydride is added to the solution under an ice bath; the temperature of the solution is recovered to room temperature; the solution is stirred for 10 to 15 hours; the reaction liquid is quenched by using water; the alcohol organic solvent is removed; the pH value of the solution is regulated to 1-2 by using strong acid; the solution is extracted by using an extractant, and a water phase is preserved; the pH value of the solution is regulated to 13-14 by using an alkali solution, such that a product B is obtained; (3) through a Swerns oxidation reaction, hydroxyl groups in the product B are oxidized into ketone groups; the product is washed; an organic phase is dried, filtered, and condensed; an ethyl acetate hydrochloride solution is added to the product until the pH value is 1-2; the product is stirred and cooled; when solid is completely precipitated, the product is filtered and dried by baking, such that 1-benzyl-piperidone hydrochloride is obtained. The invention is advantaged in low cost and safe operation.

Description

technical field [0001] The present invention relates to the synthetic method of 1-benzyl-3-piperidone hydrochloride. Background technique [0002] 1-Benzyl-3-piperidone hydrochloride is an important intermediate in the synthesis process, so the demand for 1-benzyl-3-piperidone hydrochloride shows a continuous and rapid growth trend. The synthetic route of 1-benzyl-3-piperidone hydrochloride mainly contains following two at present: [0003] (1) Using γ-butyrolactone as the raw material, 1-benzyl-3-piperidone salt is generated through six steps of benzylaminolysis, hydrolysis, esterification, condensation with ethyl bromoacetate, cyclization, and hydrolysis decarboxylation salt, the reaction process is as follows: [0004] [0005] This preparation method was published in China Journal of Pharmaceutical Industry 2004, 35 (7). The advantage is that each step of the reaction is a conventional reaction, without unconventional operations such as high temperature and high pre...

Claims

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Application Information

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IPC IPC(8): C07D211/74
Inventor 李建东
Owner 兰州博实生化科技有限责任公司
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