143612-79-7Relevant articles and documents
Practical and Scalable Manufacturing Process for a Novel Dual-Acting Serotonergic Antidepressant Vilazodone
Jin, Hongshan,Wu, Chengjun,Zhou, Shuhao,Xin, Yunting,Sun, Tiemin,Guo, Chun
, p. 1184 - 1189 (2021)
Vilazodone combines the effects of a selective serotonin reuptake inhibitor with the 5-HT1A receptor partial agonist activity. Here, we report the development of a viable and scalable process for manufacturing vilazodone that features a convergent synthetic approach, with low cost and high purity. The key indole synthesis was improved to first make up the hydrazone intermediate and then modify a pendant hydroxy group to realize a much increased overall yield. This process was successfully used to prepare >2 kg of vilazodone hydrochloride with a total yield of 56.2% and purity of 99.93%.
Alternative approach to synthesis of 3-(4-Chloro butyl)- 1H -indole-5-carbonitrile: A key intermediate of vilazodone hydrochloride, an antidepressant drug
Anitha,Reddy, B. Sudhakar,Sekhar,Reddy, K. Venugopal,Chandrasekhar
, p. 3563 - 3571 (2014)
An alternative and efficient telescopic approach to the synthesis of 3-(4-chloro butyl)-1H-indole -5-carbonitrile (2), a key intermediate in the synthesis of vilazodone hydrochloride (1), is described.
A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides
Sun, Wanwan,Chen, Xiaobei,Hu, Ying,Geng, Huihui,Jiang, Yuanrui,Zhou, Yuxin,Zhu, Wenjing,Hu, Min,Hu, Haohua,Wang, Xingyi,Wang, Xinli,Zhang, Shilei,Hu, Yanwei
supporting information, (2020/10/05)
A NaH-mediated detosylation reaction of various Ts-protected indoles, azaheterocycles, anilines and dibenzylamine was reported. The method features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.
Preparation method of vilazodone intermediate
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Paragraph 0039-0043; 0044-0047, (2020/05/11)
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.