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Method for producing N-amido piperidine hydrochlorate

A technology of aminopiperidine and carbamoylpiperidine, which is applied in the field of preparation of N-aminopiperidine hydrochloride, can solve the problems of carcinogenicity of nitrosopiperidine and easy harm to the human body, and achieve easy post-processing, Easy operation and mild reaction conditions

Inactive Publication Date: 2008-07-16
UNIV OF JINAN
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The sodium nitrite and nitrosopiperidine used in this method are carcinogenic and easy to cause harm to the human body

Method used

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  • Method for producing N-amido piperidine hydrochlorate
  • Method for producing N-amido piperidine hydrochlorate

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Dissolve 39.6 g of piperidine as a raw material in 40 ml of water, drop 50 ml of concentrated hydrochloric acid in an ice-water bath, and then add 40% sodium hydroxide solution to adjust the pH to 2.

[0020] Dissolve 31.5 g of sodium cyanate in 30 ml of water, add it into the above-mentioned piperidine solution at 10°C, and continue stirring at 20°C for 10 hours to obtain N-carbamoylpiperidine.

[0021] Cool the above-mentioned N-carbamoylpiperidine to -8°C, add aqueous sodium hydroxide solution, and adjust the pH to 13-14. After adding 386 grams of precooled sodium hypochlorite aqueous solution with a concentration of 10wt% under the same temperature conditions, react at room temperature for 15 hours, add sodium sulfite aqueous solution to destroy excess sodium hypochlorite, and after the aqueous layer is acidified with hydrochloric acid, concentrate and distill the water, using a volume of 1: 3 was recrystallized from ethanol-ethyl acetate to obtain 43.1 g of N-amino...

Embodiment 2

[0023] Dissolve 39.1 g of piperidine as a raw material in 40 ml of water, and add concentrated hydrochloric acid dropwise to adjust the pH to 4 under cooling in an ice-water bath.

[0024] Dissolve 34 grams of potassium cyanate in 56 ml of water, add to the above piperidine solution at 30°C, and continue stirring at 30°C for 8 hours to obtain N-carbamoylpiperidine.

[0025] The above-mentioned N-carbamoylpiperidine was cooled to 0°C, and an aqueous potassium hydroxide solution was added to adjust the pH to 13-14. After adding 586.8 grams of pre-cooled potassium hypobromite aqueous solution with a concentration of 12wt% under the same temperature condition, react at room temperature for 10 hours, add potassium sulfite aqueous solution to destroy excess potassium hypochlorite, after the aqueous layer is acidified with hydrochloric acid, concentrate and distill the water, use Recrystallization from ethanol-ethyl acetate with a volume ratio of 2:1 gave 34.9 g of N-aminopiperidine ...

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Abstract

The invention relates to a preparation method for N-aminopiperidine hydrochloride, particularly relating to a method for synthesizing N-aminopiperidine hydrochloride by piperidine, which is characterized in that the following steps are adopted: a piperidine reacts with a cyanate under an acidic condition to derive an N-carbamoyl piperidine; the N-carbamoyl piperidine reacts with a hypochlorite or hypobromite under a basic condition; after the N-carbamoyl piperidine is rearranged by Hoffman and treated by hydrochloric, the N-aminopiperidine hydrochloride is derived. In the preparation method of the invention, the reaction time of each step is short, the reaction condition is mild (normal temperature and normal pressure reaction at most of the time), the after-treatment is quite easy and a column chromatography is not needed; the method of the invention is a simple operated, economical, practical and safe synthetic method with a yield of more than 60 percent.

Description

technical field [0001] The invention relates to a preparation method of N-aminopiperidine hydrochloride, in particular to a method for synthesizing N-aminopiperidine hydrochloride starting from piperidine. Background technique [0002] N-aminopiperidine hydrochloride is an indispensable intermediate in the synthesis of the compound "Rimonabant". Rimonabant is a Cannabinoid RECEPTOR Antagonists. Rimona plaque blocks the action of the CBI receptor, which is part of the endocannabinoid (EC) system. The EC system is the nervous system in marijuana in the early 1990s, and then increases appetite, food intake and dependence on nicotine. In addition, the excessive activation of the EC system can also act on the surrounding tissues, causing a large amount of fat to accumulate in the adipocytes, thereby increasing body weight. Rimonabant can inhibit the over-excited EC system, reduce body weight, reduce waist circumference, and improve blood lipid and blood sugar metabolism in obe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/28C07D231/14
Inventor 冯润良宋智梅
Owner UNIV OF JINAN
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