Investigation of the phase diagrams of chiral praziquantel.
In the present work, thermal properties of praziquantel, including melting point phase diagram and solubility, were determined for the purpose of exploration on an integrated enantioseparation process of chromatography and crystallization. The solubility of racemic praziquantel in methanol and 2-propanol was measured in the temperature range between 0 and 40 degrees C. In agreement with previous conclusions, the resulting phase diagram reveals the racemic compound behavior of praziquantel arising from the existence of eutectics. A ternary phase diagram of praziquantel enantiomers and the methanol system was also determined. Based on the information provided by the ternary solubility phase diagram, an optimized integrated enantioseparation process was suggested. Pure praziquantel crystals were recovered, and the crystal structure was solved by X-ray crystallography.
Liu
Yue
Y
Department of Chemistry, National University of Singapore, Singapore. chmliuyue@gmail.com
Wang
Xin
X
Wang
Jing-Kang
JK
Ching
Chi Bun
CB
D019840:2-Propanol / Q000737:chemistry; D000871:Anthelmintics / Q000032:analysis* / Q000737:chemistry*; D003460:Crystallization; D018360:Crystallography, X-Ray; D000432:Methanol / Q000737:chemistry; D008958:Models, Molecular; D044367:Phase Transition; D011223:Praziquantel / Q000032:analysis* / Q000737:chemistry*; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D013816:Thermodynamics
D000871:Anthelmintics; D012997:Solvents; D011223:Praziquantel; D019840:2-Propanol; D000432:Methanol