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【结 构 式】 
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【药物名称】Hoe-263 【化学名称】N-[2-(Diphenylmethoxy)ethyl]-m-methoxy-N,alpha-dimethylphenethylamine hydrochloride 【CA登记号】32847-88-4 【 分 子 式 】C26H32ClNO2 【 分 子 量 】426.00344 |
【开发单位】Aventis Pharma (Originator) 【药理作用】Angina pectoris, Treatment of, CARDIOVASCULAR DRUGS, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Calcium Channel Blockers |
合成路线1
The reaction of ethanolimine (I) with m-methoxyphenylacetone (II) gives the corresponding Schiff base (III), which is reduced with H2 over Pd/C to the corresponding secondary amine (IV). Methylation of (IV) with HCHO-HCOOH yields 1-(m-methoxyphenyl)-2-(N-(2-hydroxyethyl)-N-methylaminoipropane (V), which is treated with SOCl2 to afford the 2-chloroethyl derivative (VI). Finally, this compound is condensed with benzhydrol (VII) by means of NaNH2 in refluxing benzene, and treated with HCl.
| 【1】 Lindner, E.; Ehrhart, G.; Ott, H. (Aventis Pharma AG); m-Methoxy-alpha-methyl-phenethyl-amino-diphenylmethyl ethers. US 3565955 . |
| 【2】 Mannhold, R.; HOE-263. Drugs Fut 1985, 10, 6, 458. |
| 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) | 10259 | Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol | 141-43-5 | C2H7NO | 详情 | 详情 |
| (II) | 29663 | 1-(3-methoxyphenyl)acetone | 3027-13-2 | C10H12O2 | 详情 | 详情 |
| (III) | 29664 | 2-[[(E)-2-(3-methoxyphenyl)-1-methylethylidene]amino]-1-ethanol | C12H17NO2 | 详情 | 详情 | |
| (IV) | 29665 | 2-[[2-(3-methoxyphenyl)-1-methylethyl]amino]-1-ethanol | C12H19NO2 | 详情 | 详情 | |
| (V) | 29666 | 2-[[2-(3-methoxyphenyl)-1-methylethyl](methyl)amino]-1-ethanol | C13H21NO2 | 详情 | 详情 | |
| (VI) | 29667 | N-(2-chloroethyl)-N-[2-(3-methoxyphenyl)-1-methylethyl]-N-methylamine; N-(2-chloroethyl)-1-(3-methoxyphenyl)-N-methyl-2-propanamine | C13H20ClNO | 详情 | 详情 | |
| (VII) | 11845 | Diphenylmethanol; Benzhydrol | 91-01-0 | C13H12O | 详情 | 详情 |