Method for preparing 3-methylamino piperidine and its salt

A technology of aminopyridine and alkyl, applied in the field of preparation of 3-methylaminopiperidine and its salts, can solve the problem of high cost, achieve the effects of reducing production cost, simplifying process operation, and shortening reaction steps

Active Publication Date: 2005-08-31
LIANYUNGANG RUNZHONG PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

3-Methylaminopiperidine is the key intermediate for the synthesis of baloxacin. The literature search for the synthesis method of 3-methylaminopiperidine was found in November 2004. The researchers reported the synthesis of 3-methylaminopiperidine [Chinese Journal of Pharmaceutical Industry, 2004, 35(7): 385-388]. They used γ-butyrolactone as the starting material to obtain the product through eight steps of reaction, The overall yield is 11.5%, during which the precious metal catalyst PtO was used 2 ,High cost

Method used

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  • Method for preparing 3-methylamino piperidine and its salt
  • Method for preparing 3-methylamino piperidine and its salt
  • Method for preparing 3-methylamino piperidine and its salt

Examples

Experimental program
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Effect test

Embodiment 1

[0030] In a 250ml three-necked flask, add 18.8g (0.2mol) of 3-aminopyridine and 220ml (2mol) of trimethyl orthoformate, and stir and reflux for 10h. After the reaction, the solvent was distilled off under reduced pressure. The residue was subjected to fractional distillation under reduced pressure, and the 58-60°C / 100Pa fraction was collected to obtain the compound of formula II (R 1 It is methyl) 20.4g (0.15mol) of colorless liquid, yield 75%. The TLC method followed the reaction process, the developer was ethyl acetate, observed under 254nm fluorescent lamp, the product spot R f = 0.8.

Embodiment 2

[0032] In a 250ml three-neck flask, add 18.8g (0.2mol) of 3-aminopyridine and 160ml (1.22mol) of triethyl orthoformate, and stir and reflux for 5h. After the reaction, the solvent was distilled off under reduced pressure. The residue was subjected to fractional distillation under reduced pressure, and the fraction at 60-62°C / 100Pa was collected to obtain the compound of formula II (R 1 It is ethyl) 25.5g (0.17mol) of colorless liquid, yield 85%. The TLC method followed the reaction process, the developer was ethyl acetate, observed under 254nm fluorescent lamp, the product spot R t = 0.8.

Embodiment 3

[0034] In a 250ml three-necked flask, add 18.8g (0.2mol) of 3-aminopyridine and 40ml (0.3mol) of triethyl orthoformate, and stir and reflux for 6h. After the reaction, the solvent was distilled off under reduced pressure. The residue was subjected to fractional distillation under reduced pressure, and the fraction at 60-62°C / 100Pa was collected to obtain the compound of formula II (R 1 (Ethyl) 18g of colorless liquid, yield 60%.

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Abstract

A process for preparing 3-methylamino piperidine and its salt from 3-aminopyridine includes methylation reaction to obtain 3-methylamino pyridine, reducing itin metallic sodium-alcohol system to obtain 3-methylamino piperdine, and reacting on acid to obtain its salt.

Description

technical field [0001] The present invention relates to the preparation method of the compound 3-methylaminopiperidine represented by formula (I) and salts thereof. [0002] Background technique [0003] Balofloxacin (Balofloxacin) is a fluoroquinolone antibacterial drug jointly developed by Chugai Pharmaceutical Co., Ltd. of Japan and Choongwae Company of Korea. It was first listed in South Korea at the end of 2002. ): 190-193]. The in vitro activity of this product against G+ bacteria such as methicillin-resistant S. ) similar to [Nippon Kagaku Ryoho Gakkai Zasshi, 1995, 43 (S-5): 1-9], and low phototoxicity [AntimicrobAgents Chemother, 1993, 37 (10): 2217-2223], clinically used to treat system infections. 3-Methylaminopiperidine is the key intermediate for the synthesis of baloxacin. The literature search for the synthesis method of 3-methylaminopiperidine was found in November 2004. The researchers reported the synthesis of 3-methylaminopiperidine [Chinese Journal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/56
Inventor 刘飞高勇张喜全艾建国
Owner LIANYUNGANG RUNZHONG PHARMA CO LTD
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