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【结 构 式】 
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【药物名称】Rimcazole hydrochloride, SH 1/76(monohydrochloride), BW-234U(free base) 【化学名称】cis-9-[3-(3,5-Dimethyl-1-piperazinyl)propyl]-9H-carbazole dihydrochloride 【CA登记号】75859-03-9, 75859-04-0 (free base), 75859-05-1 (monohydrochloride) 【 分 子 式 】C21H29Cl2N3 【 分 子 量 】394.39138 |
【开发单位】GlaxoSmithKline (Originator) 【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS, sigma Receptor Antagonists |
合成路线1
The reaction of 3-chloropropanol (I) with 2,6-dimethylpiperazine (II) by means of Na2CO3 in refluxing glycol monomethyl ether gives 3-(3,5-dimethyl-1-piperazinyl)propanol (III), which by reaction with refluxing SOCl2 is converted into 3-(3,5-dimethylpiperazinyl)propyl chloride (IV). Finally, this compound is condensed with carbazole (V) by means of NaH in hot DMF; a final treatment with aqueous HCl yields the dihydrochloride.
| 【1】 Harfenist, M.; Jogner, C.T. (Glaxo Wellcome Inc.); Carbazole compounds and medicinal use thereof. DD 147110; EP 0012208; EP 0051321; US 4379160 . |
| 【2】 Blancafort, P.; Hilier, K.; Serradell, M.N.; Castaner, J.; BW-234U. Drugs Fut 1983, 8, 4, 303. |
| 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) | 20848 | (2R,6S)-2,6-dimethylpiperazine | C6H14N2 | 详情 | 详情 | |
| (II) | 19490 | 3-chloro-1-propanol | 627-30-5 | C3H7ClO | 详情 | 详情 |
| (III) | 36062 | 3-[(3R,5S)-3,5-dimethylpiperazinyl]-1-propanol | C9H20N2O | 详情 | 详情 | |
| (IV) | 36063 | (3R,5S)-1-(3-chloropropyl)-3,5-dimethylpiperazine | C9H19ClN2 | 详情 | 详情 | |
| (V) | 36064 | 9H-carbazole | 86-74-8 | C12H9N | 详情 | 详情 |