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【结 构 式】 
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【药物名称】Bupropion hydrochloride, Amfebutamone hydrochloride, BW-323U66(free base), Wellbutrin XL, Quomem, Zyban, Wellbutrin, Wellbatrin 【化学名称】(±)-1-(3-Chlorophenyl)-2-(tert-butylamino)propan-1-one hydrochloride 【CA登记号】31677-93-7, 34911-55-2 (free base) 【 分 子 式 】C13H19Cl2NO 【 分 子 量 】276.20848 |
【开发单位】GlaxoSmithKline (Originator), National Institute on Drug Abuse (Not Determined), Biovail (Licensee), Esteve (Licensee), Watson (Generic) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Antidepressants, Antiobesity Drugs, Attention Deficit Hyperactivity Disorder (ADHD), Treatment of, METABOLIC DRUGS, Mood Disorders, Treatment of, Neuropathic Pain, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, Smoking Cessation, Aid to, Treatment of Nutritional Disorders, TREATMENT OF POISONING, DRUG ABUSE & DEPENDENCY, Treatment of Substance Dependency, Dopamine Reuptake Inhibitors |
合成路线1
By reaction of alpha,m-(dichloropropiophenone (I) with tert-butylamine (B) in refluxing acetonitrile or by reaction of alpha-bromo-m-chloropropiophenone (VI) with tert-butylamine (B) in acetonitrile at room temperature. The starting product (I) can be obtained in two different ways: 1) The Grignard condensation of m-chlorobenzonitrile (II) with ethyl magnesium bromide (A) in refluxing ether gives m-chloropropiophenone (III), which is then treated with SO2Cl2 in tetrachloroethane. 2) The reaction of propiophenone (IV) with SO2Cl2 in tetrachloroethane gives alpha-chloropropiophenone (V), which is then chlorinated in the ring by means of SO2Cl2 and AlCl3 in tetrachloroethane. The starting product (VI) is obtained by bromination of m-chloropropiophenone (III) with Br2 in methylene chloride
| 【1】 Mehta, N.B.; Yeowell, D.A.; Intermediates for biologically active ketones. CA 977778 . |
| 【2】 Mehta, N.B.; Yeowell, D.A.; Amino-propiophenones et medicaments contenant ces substances. DE 2059618; DE 2064934; FR 2081326; US 3819706 . |
| 【3】 Hopkins, S.J.; Castaner, J.; Bupropion. Drugs Fut 1978, 3, 10, 723. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 17895 | 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine | 75-64-9 | C4H11N | 详情 | 详情 |
| (A) | 24239 | bromo(ethyl)magnesium；ethylmagnesium bromide | 925-90-6 | C2H5BrMg | 详情 | 详情 |
| (I) | 33569 | 2-chloro-1-(3-chlorophenyl)-1-propanone | C9H8Cl2O | 详情 | 详情 | |
| (II) | 33570 | 3-chlorobenzonitrile | 766-84-7 | C7H4ClN | 详情 | 详情 |
| (III) | 33571 | 3'-chloropropiophenone; 1-(3-chlorophenyl)-1-propanone | 34841-35-5 | C9H9ClO | 详情 | 详情 |
| (IV) | 33531 | propiophenone | 93-55-0 | C9H10O | 详情 | 详情 |
| (V) | 33572 | 2-chloro-1-phenyl-1-propanone | C9H9ClO | 详情 | 详情 | |
| (VI) | 33573 | 2-bromo-1-(3-chlorophenyl)-1-propanone | C9H8BrClO | 详情 | 详情 |