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【结 构 式】 
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【分子编号】10758 【品名】1-Chloro-3-(4-phenylpiperazino)-2-propanol 【CA登记号】 |
【 分 子 式 】C13H19ClN2O 【 分 子 量 】254.75944 【元素组成】C 61.29% H 7.52% Cl 13.92% N 11% O 6.28% |
合成路线1
该中间体在本合成路线中的序号：(III)The reaction of phenylpiperazine (I) with epichlorhydrin (II) leads to 1-chloro-3-(1-phenyl-4-piperazinyl)-2-propanol. This intermediate is dehydrohalogenated to 1-(1-phenyl-4-piperazinyl)-2,3-epoxypropane (III) using sodium hydroxide. The epoxide is converted without further purification into the corresponding 4,5-dihydro-5-[(4-phenyl-1-piperazinyl)methyl]-2-oxazolamine (COR3224) by condensation with monosodium cyanamide salt in methanol, which permits the solubilization of all compounds. The amidine group of the oxazoline ring induces a tautomeric amino-imino equilibrium. For COR3224 it has been shown by X-ray crystallography that the amino form is preponderant in the free base, whereas the imino form predominates in salts.
| 【1】 Creuzet, M.-H.; Feniou, C.; Jarry, C.; Prat, G.; Pontagnier, H. (Societé Cortial SA); Novel 2-amino-5-aminomethyl-2-oxazolines. EP 0106776; FR 2546167 . |
| 【2】 D'Arnoux, C.; Panconi, E.; Descas, P.; Vaugien, B.; Lambrey, B.; Mosser, J.; Jarry, C.; Gomond, P.; Saudubray, F.; Roux, J.; COR3224. Drugs Fut 1991, 16, 10, 893. |
| 【3】 Ouhabi, J.; Jarry, C.; Bosc, J.J.; Carpy, A.; Crystal and molecular structure of 5-(1-aryl-4-piperazino)-methyl-2-amino-2-oxazolines with antidepressant activity. Arch Pharm 1990, 323, 157-61. |
| 【4】 Bosc, J.J.; Descas, P.; Carpy, A.; Panconi, E.; Jarry, C.; Synthesis and antidepressant activity of 5-(1-aryl-4-piperazino)methyl-2-amino-2-oxazolines. Eur J Med Chem 1992, 27, 5, 437. |