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【结 构 式】 
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【药物名称】Nomifensine maleate, Hoe-984, Merital 【化学名称】8-Amino-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline maleate 【CA登记号】32795-47-4, 24526-64-5 (free base) 【 分 子 式 】C20H22N2O4 【 分 子 量 】354.40934 |
【开发单位】Aventis Pharma (Originator) 【药理作用】Antidepressants, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, Dopamine Reuptake Inhibitors, Norepinephrine Reuptake Inhibitors |
合成路线1
By condensation of 2-nitrobenzylmethylamine (I) with alpha-bromoacetophenone (A) in ethanol to give omega-[N-(2-nitrobenzyl)methylamino]acetophenone (II) (HCl salt, m.p. 165-7 C), which is then reduced first with H2 over Pd/C, or Ni-diatomaceous earth and afterwards with NaBH4 in CH2Cl2 to give N-(2-aminobenzyl)-1-phenyl-2-methylaminoethanol (III), m.p. 67-9 C. This product is finally cyclized with sulfuric acid.
| 【1】 Chatterjee, S.S.; Castañer, J.; Nomifensin. Drugs Fut 1976, 1, 2, 72. |
| 【2】 Hoffmann, I.; Gustav, E.; Schmitt, K.; 8-Amino-4-phenyl-1,2,3,4-tetrahydroisoquinolines, a new group of anti-depressive psycholeptic drugs. Arzneim-Forsch Drug Res 1971, 21, 7, 1045. |
| 【3】 Hoffmann, I.; Gustav, E.; Heinrich, O.; Schmitt, K. (Aventis Pharma AG); 4-Phenyl-8-amino tetrahydroisoquinolines. DE 1670694; DE 1670848; FR 1524487; FR 6496M; FR 6646M; GB 1164192; US 3577424 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 10315 | 2-Bromo-1-phenyl-ethanone; 2-Bromo-1-phenyl-1-ethanone | 70-11-1 | C8H7BrO | 详情 | 详情 |
| (I) | 15242 | N-methyl(2-nitrophenyl)methanamine; N-methyl-N-(2-nitrobenzyl)amine | C8H10N2O2 | 详情 | 详情 | |
| (II) | 40345 | 2-[methyl(2-nitrobenzyl)amino]-1-phenyl-1-ethanone | C16H16N2O3 | 详情 | 详情 | |
| (III) | 40346 | 2-[(2-aminobenzyl)(methyl)amino]-1-phenyl-1-ethanol | C16H20N2O | 详情 | 详情 |