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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information