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Preparation method of tropisetron hydrochloride

A technology for tropisetron hydrochloride and preparation steps, which is applied in the field of preparation of tropisetron hydrochloride, can solve problems such as expensive n-butyllithium, hidden dangers in production safety, and difficulty in evaporation to dryness, and saves workload and cost. , the effect of easy operation

Inactive Publication Date: 2017-06-13
KAMP PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As shown in the following process route, the main disadvantages of this process route are: toluene has a high boiling point and is difficult to evaporate to dryness; expensive, flammable and explosive n-butyllithium is used, which brings hidden dangers to industrialized safe production; Process route: see figure 1

Method used

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  • Preparation method of tropisetron hydrochloride
  • Preparation method of tropisetron hydrochloride
  • Preparation method of tropisetron hydrochloride

Examples

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Embodiment 1

[0032] (1) Preparation of (II) ( Figure 4 ):

[0033] Add reactant (I) (50g, 0.31mol) and dichloromethane (300mL) into the reaction flask, cool down to about 0°C, then add thionyl chloride (27mL, 0.37mol) dropwise to the above reaction flask During the middle, the drop was completed, raised to room temperature and stirred for 2 hours, and TLC monitored the progress. After the reaction was complete, the reaction system was concentrated to dryness at room temperature under reduced pressure to obtain a yellow solid (II), regardless of weight and yield, which was dissolved by adding tetrahydrofuran (400mL). directly used in the next step reaction;

[0034] (2) Preparation of (IV) ( Figure 5 ):

[0035] Add (Ⅲ) (43.8g, 0.31mol), tetrahydrofuran (400mL), and triethylamine (64.5mL, 0.47mol) into the reaction flask, and add the tetrahydrofuran solution of 3-indolecarbonyl chloride prepared above to the reaction flask dropwise. In the bottle, after dropping, raise the temperature...

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Abstract

The invention discloses a preparation method of tropisetron hydrochloride. The Preparation method of the tropisetron hydrochloride is characterized by comprising the following preparation steps: (A) performing substation reaction on 3-indolecarboxylic acid (I) serving as a starting material and thionyl chloride by adding a reaction solvent to prepare 3-indoleformyl chloride (II), and directly performing condensation reaction on the 3-indoleformyl chloride (II) and alpha-tropine (III) under the existence of an acid-binding agent triethylamine to produce tropisetron (IV); and (B) performing acid and alkali salt-forming reaction on the tropisetron (IV) and hydrochloric acid in ethanol to produce the tropisetron hydrochloride (V). Raw materials used in the process reactions are the conventional reagents, are easily available on the market and are low in cost; the conditions are simple and not harsh, the conventional equipment can meet production requirements and are easy to control, and industrialized production can be realized; and dichloromethane and tetrahydrofuran have low boiling point and are easily evaporated to dryness, so energy conservation and safety are achieved.

Description

technical field [0001] The invention belongs to the field of chemical medicine synthesis, and in particular relates to a preparation method of tropisetron hydrochloride. Background technique [0002] Tropisetron hydrochloride (Tropisetron hydrochloride) chemical name -1H-indole-3 carboxylic acid-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester hydrochloride, is 5- A potent and highly selective antagonist of HT3 receptors, used to treat nausea and vomiting caused by radiotherapy and chemotherapy in children and nausea and vomiting after adult surgery. The drug was developed by Novartis and launched in the UK in 1992. [0003] 3-indolecarboxylic acid (1) was substituted with thionyl chloride to obtain 3-indolecarbonyl chloride (2), and then α-tropine alcohol (3) was treated with n-butyllithium to obtain highly active α- Lithium tropine alkoxide is then condensed with 3-indoleformyl chloride (2) to obtain tropisetron, and finally reacted with hydrochloric acid to obtain tropisetron ...

Claims

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Application Information

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IPC IPC(8): C07D451/12
CPCC07D451/12
Inventor 曾培安成中华吴健民贺莲
Owner KAMP PHARMA
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