- Microwave-Assisted Solvent-Free Synthesis of Ipsapirone
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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.
- Ku?aga, Damian,Ja?kowska, Jolanta,Jasiński, Radomir
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- Synthesis and pharmacological properties of N-(4-substituted-1-piperazinylalkyl)-1-butyl-2,5-dimethylpyrrole-3,4-d icarboxyimide derivatives
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The preparation of a number of N-(4-substituted-1-piperazinylalkyl)-1-butyl-2,5-dimethylpyrrole-3,4-d icarboxyimides (3) is described. The structures of the novel compounds were confirmed by elemental and spectral analyses. The results of a preliminary pharmacological study of CNS effects caused by compounds 3 are reported.
- Malinka,Tatarczynska
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p. 933 - 947
(2007/10/02)
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- 2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyrimidines
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1-[4-(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]piperazines with 2-pyrimidyl substituents in the 4- position have been synthesized and demonstrate useful anxiolytic properties. The compound 4,4-dimethyl-1-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,6-piperidinedione, which has selective anxiolytic activity, constitutes the preferred embodiment of the invention.
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- Spiro-quaternary ammonium halides and N-(2-pyrimidinyl)piperazinylalkylazaspiroalkanedione process
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Novel spiro-quaternary ammonium halides are disclosed. The new compounds are particularly valuable as intermediates in preparation of N-(2-pyrimidinyl)piperazinylalkyl derivatives of azaspiroalkanediones such as the psychopharmacologic agent 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione.
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