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【结 构 式】 
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【药物名称】Befuraline hydrochloride, DIV-154 【化学名称】N-Benzyl-coumarilic acid piperazide hydrochloride 【CA登记号】41717-30-0 (free base) 【 分 子 式 】C20H21ClN2O2 【 分 子 量 】356.85557 |
【开发单位】Aventis Pharma (Originator) 【药理作用】Antidepressants, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS |
合成路线1
Coumarilic acid is reacted with N-benzylpiperazine (II) by two different ways: a) The acid chloride (I) is treated with (II) in the presence of a further base to give (III) or without a base in boiling dimethylformamide. b) The coumarilic acid salt of N-benzylpiperazine (IV) is converted to (III) by heating up to 170-250 C.
| 【1】 Boksay, I.J.E.; et al.; Synthesis and pharmacological activity of befuralline, a new antidepressnt compound. Arzneim-Forsch Drug Res 1978, 28, 19, Suppl. 2. |
| 【2】 Soeder, A.; et al. (Aventis Pharma AG); Cyclic diamine derivatives. DE 2157424; DE 2240665; ES 408565; FR 2160611; GB 1407854; US 4374990 . |
| 【3】 Unterhalt, B.; Befuraline Hydrochloride. Drugs Fut 1978, 3, 6, 426. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 39812 | 1-benzofuran-2-carbonyl chloride | 41717-28-6 | C9H5ClO2 | 详情 | 详情 |
| (II) | 28542 | N-Benzylpiperazine; 1-Benzylpiperazine | 2759-28-6 | C11H16N2 | 详情 | 详情 |
| (III) | 39813 | 1-benzofuran-2-yl(4-benzyl-1-piperazinyl)methanone | C20H20N2O2 | 详情 | 详情 | |
| (IV) | 39814 | 1-benzylpiperazin-4-ium 1-benzofuran-2-carboxylate | C20H22N2O3 | 详情 | 详情 |