Method of synthesizing 3-quininone hydrochlorate

A technology of quinine hydrochloride and synthesis method, which is applied in the direction of organic chemistry, etc., can solve problems such as inconvenient operation, and achieve the effects of simple method, high yield and low cost

Inactive Publication Date: 2007-08-08
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Bibliographical reports (Organic Syntheses, Coll.Vol.5, p.989 (1973); Vol.44, p.86 (1964).) take 4-picolinic acid as raw material through multi-step synthesis, adopted high temperature and high pressure in the route, Inconvenient to operate

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  • Method of synthesizing 3-quininone hydrochlorate
  • Method of synthesizing 3-quininone hydrochlorate
  • Method of synthesizing 3-quininone hydrochlorate

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Effect test

Embodiment 1

[0041] The synthetic method of 3-quininone hydrochloride is realized through the following steps:

[0042] 1) Preparation of ethyl 4-piperidinecarboxylate hydrochloride

[0043] Add 12.9g (0.1mol) of 4-piperidinecarboxylic acid and 150ml of absolute ethanol to a 250ml one-port bottle, and slowly add 30ml (0.3mol) of thionyl chloride dropwise at 0°C. The whole dropping process lasts for 1 hour. After the dropping, Raise the temperature and reflux for 6h, concentrate under reduced pressure to remove the solvent, add saturated NaOH solution to the residual solid to adjust to strong alkalinity, extract with 3×100ml chloroform, and dry the organic layer with calcium chloride; concentrate under reduced pressure to remove the solvent, and the residual Dissolve the solution in 100ml of absolute ethanol; pass hydrogen chloride gas into the ethanol, stir at 0°C for 0.5h, filter, and dry in vacuo to obtain 18.3g of white solid with a yield of 95%.

[0044] Mp: 142-145°C,

[0045] 1 H ...

Embodiment 2

[0056] The synthetic method of 3-quininone hydrochloride is realized through the following steps:

[0057] 1) Preparation of ethyl 4-piperidinecarboxylate hydrochloride

[0058] Add 12.9g (0.1mol) of 4-piperidinecarboxylic acid and 150ml of absolute ethanol to a 250ml one-port bottle, and slowly add 30ml (0.3mol) of thionyl chloride dropwise at 0°C. The whole dropping process lasts for 1 hour. After the dropping, Raise the temperature and reflux for 6h, concentrate under reduced pressure to remove the solvent, add saturated NaOH solution to the residual solid to adjust to strong alkalinity, extract with 3×100ml chloroform, and dry the organic layer with calcium chloride; concentrate under reduced pressure to remove the solvent, and the residual Dissolve the solution in 100ml of absolute ethanol; pass hydrogen chloride gas into the ethanol, stir at 0°C for 0.5h, filter, and dry in vacuo to obtain 18.3g of white solid with a yield of 95%.

[0059] MP: 142-145°C

[0060] 1 H N...

Embodiment 3

[0070] The synthetic method of 3-quininone hydrochloride is realized through the following steps:

[0071] 1) Preparation of ethyl 4-piperidinecarboxylate hydrochloride

[0072] Add 12.9g (0.1mol) of 4-piperidinecarboxylic acid and 150ml of absolute ethanol to a 250ml one-port bottle, and slowly add 30ml (0.3mol) of thionyl chloride dropwise at 0°C. The whole dropping process lasts for 1 hour. After the dropping, Raise the temperature and reflux for 6h, concentrate under reduced pressure to remove the solvent, add saturated NaOH solution to the residual solid to adjust to strong alkalinity, extract with 3×100ml chloroform, and dry the organic layer with calcium chloride; concentrate under reduced pressure to remove the solvent, and the residual Dissolve the solution in 100ml of absolute ethanol; pass hydrogen chloride gas into the ethanol, stir at 0°C for 0.5h, filter, and dry in vacuo to obtain 18.3g of white solid with a yield of 95%.

[0073] MP: 142-145°C

[0074] 1 H N...

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Abstract

The invention discloses a synthesizing method of 3-quininone hydrochlorate, which comprises the following steps: adopting 4-piperidine aminic acid as raw material; esterifying; proceeding N-hydrocarbonization through halogenated acetic ester; obtaining diester catalyzed by alkaline to do Dieckmann condensation; stripping ester in the condensed acid condition to obtain the product.

Description

technical field [0001] The invention relates to a synthesis method of 3-quininone hydrochloride, which belongs to the technical field of organic chemistry and also belongs to the technical field of medicinal chemistry. Background technique [0002] 3-Quiningone hydrochloride is the precursor of chiral ligands, from which chiral ligands can be synthesized for asymmetric catalysis; it is also an important raw material for the synthesis of antiemetic drugs. Since the 1970s, the synthesis of antiemetics has been the focus of attention and research hotspot in the pharmaceutical industry at home and abroad. [0003] Bibliographical reports (Organic Syntheses, Coll.Vol.5, p.989 (1973); Vol.44, p.86 (1964).) take 4-picolinic acid as raw material through multi-step synthesis, adopted high temperature and high pressure in the route, Inconvenient to operate. Therefore, people have been looking for simple, safe, and low-cost production methods, thereby reducing production costs and be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D453/04
Inventor 申永存滕汉兵王平
Owner WUHAN UNIV OF TECH
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