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Process for preparing N-amino piperidine hydrochloride

A technology for the preparation of aminopiperidine, applied in the field of preparation of N-aminopiperidine hydrochloride, capable of solving problems such as long reaction time, high temperature and pressure, and long reaction time

Inactive Publication Date: 2006-05-24
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The operation steps of this invention are not very complicated, but the reaction time is relatively long, and it needs to be heated for a long time
And European patent Eur.Pat.Appl.Ep 845438 needs higher temperature and pressure, also needs very long reaction time

Method used

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  • Process for preparing N-amino piperidine hydrochloride
  • Process for preparing N-amino piperidine hydrochloride
  • Process for preparing N-amino piperidine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Dissolve 39.6ml of piperidine in 40ml of water, under ice bath cooling, slowly add 85ml of concentrated hydrochloric acid dropwise, then add 250ml of organic solvent ethyl acetate, dissolve 27.6g of sodium nitrite in water, drop into the reaction solution, add dropwise The time was 2 hours, and the ice bath continued to stir for 30 minutes, and then 13.8g of sodium nitrite was dissolved in water and dropped into the reaction solution; naturally rose to room temperature and stirred, and after 2 hours of reaction, the reaction color changed from green to yellow, and the reaction was stopped. The layers were separated, the aqueous layer was back-extracted twice with ethyl acetate, the organic layers were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, and concentrated to dryness to obtain 38.7 g of the compound nitrosopiperidine as a yellow oily liquid with a yield of 84.8 %;

[0015] In a dry 250ml single-necked bottle, add 50ml of anhydro...

Embodiment 2

[0017] Dissolve 120ml of piperidine in 120ml of water, under ice bath cooling, slowly add 260ml of concentrated hydrochloric acid dropwise, then add 750ml of organic solvent chloroform, dissolve 82.8g of sodium nitrite in water, drop into the reaction solution, dropwise for 1 hour 40 Continue to stir in the ice bath for 30 minutes, then dissolve 41.6g of sodium nitrite in water, drop into the reaction solution; naturally rise to room temperature and stir, after 2.5 hours of reaction, the reaction color turns from green to yellow, stop the reaction, and separate layers , the aqueous layer was back-extracted twice with chloroform, the combined organic layers were washed once with saturated brine, dried over anhydrous sodium sulfate, and concentrated to dryness to obtain 115.8 g of compound nitrosopiperidine as a yellow oily liquid with a yield of 83.49%;

[0018] In a dry 1000ml single-necked bottle, add 150ml of ether and 3.42g of lithium aluminum tetrahydride under ice bath, di...

Embodiment 3

[0020] Dissolve 39.6ml of piperidine in 40ml of water, under ice bath cooling, slowly add 85ml of concentrated hydrochloric acid dropwise, then add 250ml of organic solvent toluene, dissolve 27.6g of sodium nitrite in water, drop into the reaction solution, dropwise for 2 After 3 hours, the ice bath continued to stir for 30 minutes, then 13.8g of sodium nitrite was dissolved in water and dropped into the reaction solution; naturally rose to room temperature and stirred, and after 3 hours of reaction, the reaction color changed from green to yellow, the reaction was stopped, and the layers were separated. , the aqueous layer was back-extracted twice with toluene, the organic layers were combined, and washed once with saturated brine; dried over anhydrous sodium sulfate, and concentrated to dryness to obtain 38.7 g of compound nitrosopiperidine as a yellow oily liquid, with a yield of 84.8%;

[0021] Add 1.68g of iron filings, 0.5ml of concentrated hydrochloric acid and 20ml of w...

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Abstract

The invention relates to a technique for preparing N-amino piperidine hydrochloride, making piperidine react with sodium nitrite under acidic condition to produce nitroso piperidine, reducing the nitroso piperidine with reducer and obtaining the target compound N-amino piperidine hydrochloride by HCl processing. The reacting time for each step is shorter, the reacting conditions are moderate, the after processing is extremely easy, and it needs no chromatographic column, and it is a synthesizing method simple and convenient to operate, economic and practical.

Description

technical field [0001] The invention relates to a preparation process of N-aminopiperidine hydrochloride Background technique [0002] N-aminopiperidine hydrochloride is an indispensable intermediate in the synthesis of the compound "Rimonabant". Rimonabant is a Cannabinoid RECEPTOR Antagonists. Rimonabant blocks the action of the CB1 receptor, which is part of the endocannabinoid (EC) system. The EC system was discovered in the early 90s during research on the neuroactive substance THC in cannabis. If the EC system is overactivated, it can act on the central nervous system, thereby increasing 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 ...

Claims

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Application Information

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IPC IPC(8): C07D211/98
Inventor 高巍刘锦轮彭新湘廖立新
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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