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【结 构 式】 
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【分子编号】22872 【品名】1-(4-chlorophenyl)cyclobutanecarbonitrile 【CA登记号】 |
【 分 子 式 】C11H10ClN 【 分 子 量 】191.65984 【元素组成】C 68.94% H 5.26% Cl 18.5% N 7.31% |
合成路线1
该中间体在本合成路线中的序号：(II)4-Chlorobenzyl cyanide (I) is cycloalkylated with 1,3-dibromopropane to yield 1-(4-chlorophenyl)cyclobutyl cyanide (II). The cyclobutyl cyanide (II) is treated with 2-methylpropyl magnesium bromide te give the imine salt (III), which may be either hydrolyzed to the ketone (IV), which is then formylaminated with formamide and formic acid and subsequently hydrolyzed, or reduced with sodium borohydride in ethanol to give 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine (V). Eschweiler-Clarke methylation and hydrochloride formation yield N-[1-[1-(4-chlorophenyl)cyclo butyl]-3-methylbutyl]-N,N-dimethylamine hydrochloride monohydrate
| 【1】 Jeffery, J.E.; Kozlik, A.; Wilmshurst, E.C. (The Boots Company plc); Substd. cyclobutanes, process for their preparatio. DE 3212682; GB 2098602; US 4806570 . |
| 【2】 Jeffery, J.E. (The Boots Company plc); N,N-Dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-me. GB 2184122; US 4929629 . |
| 【3】 Buckett, W.R.; Harris, P.J.; SIBUTRAMINE HYDROCHLORIDE < Rec INN; BAN >. Drugs Fut 1988, 13, 8, 736. |
| 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) | 22876 | bromo(isobutyl)magnesium | 926-62-5 | C4H9BrMg | 详情 | 详情 |
| (I) | 22871 | 2-(4-chlorophenyl)acetonitrile | 140-53-4 | C8H6ClN | 详情 | 详情 |
| (II) | 22872 | 1-(4-chlorophenyl)cyclobutanecarbonitrile | C11H10ClN | 详情 | 详情 | |
| (III) | 22873 | 1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutylideneamine bromomagnesium salt | C15H19BrClMgN | 详情 | 详情 | |
| (IV) | 22874 | 1-[1-(4-chlorophenyl)cyclobutyl]-3-methyl-1-butanone | C15H19ClO | 详情 | 详情 | |
| (V) | 22875 | 1-[1-(4-chlorophenyl)cyclobutyl]-3-methyl-1-butanamine; 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine | 84467-54-9 | C15H22ClN | 详情 | 详情 |