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【结 构 式】 
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【分子编号】14136 【品名】2-[4-[4-(4-Chloro-1H-pyrazol-1-yl)butyl]piperazino]pyrimidine 【CA登记号】 |
【 分 子 式 】C15H21ClN6 【 分 子 量 】320.82488 【元素组成】C 56.16% H 6.6% Cl 11.05% N 26.2% |
合成路线1
该中间体在本合成路线中的序号：(V)Lesopitron dihydrochloride was obtained following two related procedures. 1) Reaction of 4-chloropyrazole (I) with 1,4-dibromobutane (II) gives 1-(4-bromobutyl)-4-chloropyrazole (III). Compound (III) is refluxed with 2-(1-piperazinyl)pyrimidine (IV) and potassium carbonate in DMF to give lesopitron (V), which is treated with isopropyl alcohol saturated with hydrochloric acid to pH 4.5-5 . 2) 2-(1-Piperazinyl)pyrimidine (IV) reacts with 1,4-dibromobutane (II) to yield 8-(2-pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane bromide (VI). The quaternary salt (VI) undergoes reaction with 4-chloropyrazole (I) in DMF in the presence of potassium carbonate to afford the free base.
| 【1】 Merce-Vidal, R.; Frigola-Constansa, J.; Pares-Corominas, J. (Laboratorios del Dr. Esteve, SA); Process for the preparation of aryl (or heteroaryl) piperazinylbutylazole derivs. AU 9211429; CA 2062468; EP 0502786; ES 2036145; FR 2673628; JP 1993078313; NO 9200888; US 5227486; ZA 9201682 . |
| 【2】 Frigola, J.; Farré, A.; Lesopitron Dihydrochloride. Drugs Fut 1994, 19, 7, 651. |
| 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) | 14132 | 4-Chloro-1H-pyrazole | 15878-00-9 | C3H3ClN2 | 详情 | 详情 |
| (II) | 11883 | 1,4-Dibromobutane; 1,4-Butylene bromide | 110-52-1 | C4H8Br2 | 详情 | 详情 |
| (III) | 14134 | 1-(4-Bromobutyl)-4-chloro-1H-pyrazole | C7H10BrClN2 | 详情 | 详情 | |
| (IV) | 11175 | 2-(1-Piperazinyl)pyrimidine; 2-Piperazinopyrimidine; N-(Pyrimidinyl)piperazine | 20980-22-7 | C8H12N4 | 详情 | 详情 |
| (V) | 14136 | 2-[4-[4-(4-Chloro-1H-pyrazol-1-yl)butyl]piperazino]pyrimidine | C15H21ClN6 | 详情 | 详情 | |
| (VI) | 14137 | 8-(2-Pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane | C12H19N4 | 详情 | 详情 |