Microwave‐assisted solvent‐free synthesis of ipsapirone
Authors:
- Damian Kułaga,
- Jolanta Jaśkowska,
- Radomir Jasiński
Abstract
The currently applied synthetic methods of serotonin receptor ligands belonging to the group of long‐chain arylpiperazines, including ipsapirone, require the use of toxic solvents and comprise numerous synthetic steps. Moreover, the reaction yield does not exceed 60% in the majority of cases. These factors lead to an increased energy consumption and negatively impact the environment. This paper describes a more environmentally friendly method of ipsapirone synthesis that we decided to use. Ipsapirone was obtained in two different methods. The first method involved N‐alkylation of bromobutyl saccharin with 1‐(2‐pyrimidyl)piperazine dihydrochloride, while the second was a one‐pot method. Neither of these requires the use of toxic and expensive solvents. A shortened synthesis time, not exceeding 10 min due to the use of microwave radiation, is also another advantage of these methods. The yield of the final product, ipsapirone, was 85% and 67% in the first and the second method, respectively. We also attempted to obtain ipsapirone using saccharin and arylpiperazine salt (method III) as starting materials, but to no avail in the tested conditions. As described herein, the green chemistry method for ipsapirone synthesis is rapid, cost‐effective, and environment friendly.
- Record ID
- CUTe49de900d6f24f78a6a23f56d763686c
- Publication categories
- ;
- Author
- Journal series
- Journal of Heterocyclic Chemistry, ISSN 0022-152X, e-ISSN 1943-5193
- Issue year
- 2019
- Vol
- 56
- No
- 5
- Pages
- 1498-1504
- Other elements of collation
- rys.; schem.; tab.; wykr.; Bibliografia (na s.) - 1503-1504; Bibliografia (liczba pozycji) - 30; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 56, Iss. 5
- Keywords in English
- ipsapiron
- DOI
- DOI:10.1002/jhet.3520 Opening in a new tab
- URL
- https://onlinelibrary.wiley.com/doi/full/10.1002/jhet.3520 Opening in a new tab
- Related project
- Synteza i ocena aktywności nowych ligandów działających na receptory ośrodkowego układu nerwowego (oun). . Project leader at PK: , ,
Projects financed by NCRD [Projekty finansowane przez NCBiR (NCBR (] - Language
- eng (en) English
- Score (nominal)
- 40
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUTe49de900d6f24f78a6a23f56d763686c/
- URN
urn:pkr-prod:CUTe49de900d6f24f78a6a23f56d763686c
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.