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【结 构 式】 
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【分子编号】22937 【品名】2-[(1-naphthyloxy)methyl]oxirane; 1-naphthyl 2-oxiranylmethyl ether 【CA登记号】 |
【 分 子 式 】C13H12O2 【 分 子 量 】200.23708 【元素组成】C 77.98% H 6.04% O 15.98% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 1-(1-propen-2-yl)-2 benzimidazolinone (I) in hexamethylphosphorus triamide with sodium hydride and 3-benzalamino-3,3-dimethylpropyl chloride (II) and treating the reaction product with hydrochloric acid gives 1-(3 amino-3,3-dimethylpropyl)-2 benzimidazolone (III). The amine (III) is refluxed with 1-(1-naphthyloxy)propylene-(2,3)-oxide (IV) yielding the title compound.
| 【1】 Hoefke, W.; et al. (Boehringer Ingelheim GmbH); 1-Aryloxy-2-hydroxy-3-[(benzimidazolin-one-substituted alkyl)-amino]-propanes and salts thereof. DE 2644833 . |
| 【2】 Mentrup, A.; Palluk, R.; Gaida, W.; Hoefke, W.; Adimolol hydrochloride hydrate. Drugs Fut 1986, 11, 1, 9. |
| 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) | 24246 | 1-isopropenyl-1,3-dihydro-2H-benzimidazol-2-one | C10H10N2O | 详情 | 详情 | |
| (II) | 24247 | 4-chloro-2-methyl-N-[(E)-benzylidene]-2-butanamine | C12H16ClN | 详情 | 详情 | |
| (III) | 24248 | 1-(3-amino-3-methylbutyl)-1,3-dihydro-2H-benzimidazol-2-one | C12H17N3O | 详情 | 详情 | |
| (IV) | 22937 | 2-[(1-naphthyloxy)methyl]oxirane; 1-naphthyl 2-oxiranylmethyl ether | C13H12O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)The reaction of 1-naphthol (I) with epichlorohydrin (II) in the presence of aqueous sodium hydroxide yields 1-(1-naphthyloxy)-2,3-epoxypropane (III). (III) is then reacted either in alcohol or without any solvent with 1-(2-methoxyphenyl)piperazine (IV).
| 【1】 Thiel, M.; Sponer, G.; Stach, K.; Witte, E.-C.; Roesch, E. (Roche Diagnostics GmbH); 1-[3-(Napht-1-yloxy)-2-hydroxypropyl]-piperazine c. GB 1445548; US 3997666 . |
| 【2】 Prous, J.; Castaner, J.; Naftopidil. Drugs Fut 1987, 12, 1, 31. |
| 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) | 22935 | alpha-naphthol; 1-naphthol | 90-15-3 | C10H8O | 详情 | 详情 |
| (II) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (III) | 22937 | 2-[(1-naphthyloxy)methyl]oxirane; 1-naphthyl 2-oxiranylmethyl ether | C13H12O2 | 详情 | 详情 | |
| (IV) | 11882 | 1-(2-Methoxyphenyl)piperazine; Methyl 2-piperazinophenyl ether; 1-(2-Methoxyphenyl)-piperazine | 35386-24-4 | C11H16N2O | 详情 | 详情 |