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Preparation method of vilazodone intermediate

A technology for vilazodone and intermediates, which is applied in the field of chemical pharmacy, can solve the problems of difficulty in purchasing and preparing reagents, unstable chemical properties, and high requirements for reaction equipment, and achieves easy post-processing, stable product quality, and cheap and easy-to-obtain reagents. Effect

Active Publication Date: 2020-05-01
SHANGHAI INST OF TECH
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

Both the F-C acylation and reduction reactions of this method use Lewis acid isobutylaluminum chloride as a catalyst. This reagent is difficult to purchase and prepare, and its chemical properties are unstable, and it is extremely flammable in the air, so it needs to be transported by pipeline. , high requirements for reaction equipment

Method used

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  • Preparation method of vilazodone intermediate
  • Preparation method of vilazodone intermediate
  • Preparation method of vilazodone intermediate

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preparation example Construction

[0029] A kind of preparation method of vilazodone intermediate, this method takes compound 1 raw material, under the action of anhydrous zinc chloride and 1-bromo-4-chlorobutane (compound 3) generation F-C alkylation reaction, one-step reaction Compound I is obtained, which is the vilazodone intermediate;

[0030] The chemical structural formulas of Compound 1 and Compound I are as follows:

[0031]

[0032] The reaction formula is as follows:

[0033]

[0034] Preferably, the reaction temperature is -10-30°C, and the reaction time is 1-3h. Further preferably, the reaction temperature is 0° C., and the reaction time is 2 hours.

[0035] Preferably, the molar ratio of 1-bromo-4-chlorobutane (compound 3) to compound 1 is 1.5-1:1. Further preferably, the molar ratio of 1-bromo-4-chlorobutane (compound 3) to compound 1 is 1.1:1.

[0036] Preferably, the molar ratio of anhydrous zinc chloride to compound 1 is 1.5-1:1. Further preferably, the molar ratio of anhydrous zinc...

Embodiment 1

[0040] The preparation of 3-(4-chlorobutyl) indole-5-carbonitrile (compound I), its reaction formula is as follows:

[0041]

[0042] Compound 1 (142.2g, 1.0mol) was dissolved in dichloromethane (1.5L), and the internal temperature was controlled at 0-5°C, and anhydrous zinc chloride (150g, 1.1mol) was added. After the addition, the temperature was lowered to about -10°C, and the dropwise addition of 1-bromo-4-chlorobutane (compound 3) (188.6g, 1.1mol) was started. During the dropping process, the inner temperature was controlled below -5°C. After the addition was completed, the temperature was raised to the reaction temperature of 0° C., and the reaction was carried out for 2 hours. After the reaction was completed, dichloromethane (0.5 L) was diluted, ice water (1 L) was destroyed, then 1N sodium hydroxide solution was added to neutralize the pH=7, extraction and liquid separation were performed. The organic phase was washed with saturated brine (0.5 L) and separated. A...

Embodiment 2～4

[0045] Intermediate I was prepared by the above method, and the reaction conditions and results are shown in Table 1.

[0046] Table 1 embodiment 2~4 reaction conditions and result summary

[0047]

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Abstract

The invention relates to a preparation method of a vilazodone intermediate, which comprises the following steps: carrying out F-C alkylation reaction on a compound 1 raw material and 1-bromo-4-chlorobutane under the action of anhydrous zinc chloride, and carrying out one-step reaction to obtain a compound I, namely, the vilazodone intermediate. Compared with the prior art, the method has the advantages of short reaction route, easiness in post-treatment, high yield, cheap and easily available reagents used in the F-C reaction, convenience in operation, simplicity in post-treatment, low cost, small environmental pollution and suitability for industrial production of the vilazodone intermediate I.

Description

technical field [0001] The invention relates to the technical field of chemical industry and pharmacy, in particular to a preparation method of a vilazodone intermediate. Background technique [0002] Vilazodone (Vilazodone) was approved by the FDA for marketing in the United States on January 21, 2011. It is the first 5-HT reuptake and 5-HT drug currently on the market. 1A Some agonistic antidepressants. As a new dual-target antidepressant, vilazodone has the characteristics of rapid onset of action and no sexual dysfunction. Experts in the industry are all optimistic about its market prospects after its launch. The development of this drug in the domestic market can provide a good treatment option for the majority of depression patients and create huge social and economic value. The chemical structure of vilazodone is shown below. [0003] [0004] There are many documents (Journal of Medicinal Chemistry, 2004, 47 (19): 4684-4692; Chinese patent CN1140171A) report on...

Claims

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Application Information

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IPC IPC(8): C07D209/10
CPCC07D209/10
Inventor 方亚辉李会霞
Owner SHANGHAI INST OF TECH
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