A new synthetic ultrasound-assisted method for dibenzoepines
In this study, we have developed a new ultrasonic synthesis method of dibenzoepines using olanzapine and quetiapine, which are well-known drugs for the treatment of schizophrenia and bipolar disorder. The method is based on the N-alkylation reaction of the piperazine fragment in tricyclic compounds...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-07-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844023055275 |
| _version_ | 1797771339635884032 |
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| author | Jolanta Jaśkowska Anna Karolina Drabczyk Damian Kułaga Przemysław Zaręba Zbigniew Majka Przemysław Jodłowski |
| author_facet | Jolanta Jaśkowska Anna Karolina Drabczyk Damian Kułaga Przemysław Zaręba Zbigniew Majka Przemysław Jodłowski |
| author_sort | Jolanta Jaśkowska |
| collection | DOAJ |
| description | In this study, we have developed a new ultrasonic synthesis method of dibenzoepines using olanzapine and quetiapine, which are well-known drugs for the treatment of schizophrenia and bipolar disorder. The method is based on the N-alkylation reaction of the piperazine fragment in tricyclic compounds with methyl iodide or 2-(2-chloroethoxy)ethanol as the alkylating agent, respectively. The synthesis reactions were carried out in an ultrasonic bath with solvents such as acetonitrile or dimethylformamide in the presence of potassium or sodium carbonate or sodium hydroxide and metal-free, ecological phase transfer catalyst at a temperature of 40–50 °C. This allowed us to obtain olanzapine in 1 h (Y = 67%), and quetiapine in 3 h (Y = 72%). An ultrasonic reactor (Qsonica Q700) was used in the synthesis of olanzapine and made it possible to shorten the reaction time to 10 min and obtain 90% yield with very high purity. The developed method allows obtaining compounds in mild conditions and in a short time, thanks to which the process is more ecological than others described in the literature. |
| first_indexed | 2024-03-12T21:36:07Z |
| format | Article |
| id | doaj.art-048b6ea3e4a94046913eb41ee4ab5d75 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-03-12T21:36:07Z |
| publishDate | 2023-07-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-048b6ea3e4a94046913eb41ee4ab5d752023-07-27T05:59:15ZengElsevierHeliyon2405-84402023-07-0197e18319A new synthetic ultrasound-assisted method for dibenzoepinesJolanta Jaśkowska0Anna Karolina Drabczyk1Damian Kułaga2Przemysław Zaręba3Zbigniew Majka4Przemysław Jodłowski5Department of Organic Chemistry and Technology, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. 24 Warszawska, 31-155 Cracow, Poland; Corresponding author.Department of Organic Chemistry and Technology, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. 24 Warszawska, 31-155 Cracow, PolandDepartment of Organic Chemistry and Technology, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. 24 Warszawska, 31-155 Cracow, PolandDepartment of Chemical Technology and Environmental Analytics, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. 24 Warszawska, Cracow, 31-155, PolandDepartment of Analytical Chemistry and Biomaterials, Faculty of Pharmacy, Medical University of Warsaw, ul. Banacha 1, 02-093 Warsaw, PolandDepartment of Organic Chemistry and Technology, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. 24 Warszawska, 31-155 Cracow, PolandIn this study, we have developed a new ultrasonic synthesis method of dibenzoepines using olanzapine and quetiapine, which are well-known drugs for the treatment of schizophrenia and bipolar disorder. The method is based on the N-alkylation reaction of the piperazine fragment in tricyclic compounds with methyl iodide or 2-(2-chloroethoxy)ethanol as the alkylating agent, respectively. The synthesis reactions were carried out in an ultrasonic bath with solvents such as acetonitrile or dimethylformamide in the presence of potassium or sodium carbonate or sodium hydroxide and metal-free, ecological phase transfer catalyst at a temperature of 40–50 °C. This allowed us to obtain olanzapine in 1 h (Y = 67%), and quetiapine in 3 h (Y = 72%). An ultrasonic reactor (Qsonica Q700) was used in the synthesis of olanzapine and made it possible to shorten the reaction time to 10 min and obtain 90% yield with very high purity. The developed method allows obtaining compounds in mild conditions and in a short time, thanks to which the process is more ecological than others described in the literature.http://www.sciencedirect.com/science/article/pii/S2405844023055275Ultrasound-assisted synthesisDibenzoazepinePhase transfer catalysisN-alkylationOlanzapineQuetiapine |
| spellingShingle | Jolanta Jaśkowska Anna Karolina Drabczyk Damian Kułaga Przemysław Zaręba Zbigniew Majka Przemysław Jodłowski A new synthetic ultrasound-assisted method for dibenzoepines Heliyon Ultrasound-assisted synthesis Dibenzoazepine Phase transfer catalysis N-alkylation Olanzapine Quetiapine |
| title | A new synthetic ultrasound-assisted method for dibenzoepines |
| title_full | A new synthetic ultrasound-assisted method for dibenzoepines |
| title_fullStr | A new synthetic ultrasound-assisted method for dibenzoepines |
| title_full_unstemmed | A new synthetic ultrasound-assisted method for dibenzoepines |
| title_short | A new synthetic ultrasound-assisted method for dibenzoepines |
| title_sort | new synthetic ultrasound assisted method for dibenzoepines |
| topic | Ultrasound-assisted synthesis Dibenzoazepine Phase transfer catalysis N-alkylation Olanzapine Quetiapine |
| url | http://www.sciencedirect.com/science/article/pii/S2405844023055275 |
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