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【结 构 式】

【分子编号】12395

【品名】N-Methyl-N-(4-nitrophenethyl)amine; N-Methyl-2-(4-nitrophenyl)-1-ethanamine

【CA登记号】

【 分 子 式 】C9H12N2O2

【 分 子 量 】180.20656

【元素组成】C 59.99% H 6.71% N 15.55% O 17.76%

与该中间体有关的原料药合成路线共 3 条

合成路线1

该中间体在本合成路线中的序号:(I)

This compound can be prepared by several related ways: 1) The condensation of N-methyl-2-(4-nitrophenyl)ethylamine (I) with 4-(2-chloroethoxy)nitrobenzene (II) by means of NaI and K2CO3 in refluxing acetonitrile gives 1-(4-nitrophenoxy)-5-(4-nitrophenyl)-3-methyl-3-azapentane (III), which is reduced with H2 over Pd/C in ethanol, yielding the corresponding diamino derivative (IV). Finally, this compound is acylated with methanesulfonyl anhydride in dichloromethane. 2) The condensation of (I) with N-[4-(2-chloroethoxy)phenyl]methanesulfonamide (V) with NaI and K2CO3 as before gives 1-[4-(methanesulfonamide)phenoxy]-3-methyl-5-(4-nitrophenyl)-3-azapentane (VI), which is reduced with H2 over Pd/C as before, yielding the corresponding amino derivative (VII). Finally, this compound is acylated with methanesulfonyl anhydride as usual. 3) The condensation of (II) with N-[4-[2-(methylamino)ethyl]phenyl]methanesulfonamide (VIII) with NaI and K2CO3 as usual gives 1-[4-(methanesulfonamido)phenyl]-3-methyl-5-(4-nitrophenoxy)-3-azapentane (IX), which is reduced with H2 and RaNi to the corresponding amino derivative (X). Finally, this compound is acylated with methanesulfonyl chloride and pyridine. 4) By condensation of N-[4-[2-(methanesulfonyloxy)ethyl]phenyl]methanesulfonamide (XI) with N-[4-[2-(methylamino)ethoxy]phenyl]methanesulfonamide (XII) in refluxing ethanol. 5) By condensation of (V) with (VIII) by means of NaHCO3.

1 Arrowsmith, J.E.; Cross, P.E.; Thomas, G.N. (Pfizer Inc.); N-Substituted p-aminoethylsulphonanilides as antiarrhythmic agents, and intermediates therefor. EP 0245997; JP 1987267250; US 4959366; US 5079248 .
2 Cross, P.E.; Thomas, G.N.; Gwilt, M.; Arrowsmith, J.E.; Burges, R.A.; Selective class III antiarrhythmic agents. 1. Bis(arylalkyl)amines. J Med Chem 1990, 33, 4, 1151-5.
3 Castaner, J.; Prous, J.; UK-68,798. Drugs Fut 1991, 16, 6, 521.
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) 12395 N-Methyl-N-(4-nitrophenethyl)amine; N-Methyl-2-(4-nitrophenyl)-1-ethanamine C9H12N2O2 详情 详情
(II) 12396 2-Chloroethyl 4-nitrophenyl ether; 1-(2-Chloroethoxy)-4-nitrobenzene 3383-72-0 C8H8ClNO3 详情 详情
(III) 12397 N-Methyl-N-(4-nitrophenethyl)-2-(4-nitrophenoxy)-1-ethanamine; N-Methyl-N-(4-nitrophenethyl)-N-[2-(4-nitrophenoxy)ethyl]amine C17H19N3O5 详情 详情
(IV) 12398 N-(4-Aminophenethyl)-N-[2-(4-aminophenoxy)ethyl]-N-methylamine; 4-[2-[(4-Aminophenethyl)(methyl)amino]ethoxy]aniline C17H23N3O 详情 详情
(V) 12399 N-[4-(2-Chloroethoxy)phenyl]methanesulfonamide C9H12ClNO3S 详情 详情
(VI) 12400 N-(4-[2-[Methyl(4-nitrophenethyl)amino]ethoxy]phenyl)methanesulfonamide C18H23N3O5S 详情 详情
(VII) 12401 N-(4-[2-[(4-Aminophenethyl)(methyl)amino]ethoxy]phenyl)methanesulfonamide C18H25N3O3S 详情 详情
(VIII) 12402 N-[4-[2-(Methylamino)ethyl]phenyl]methanesulfonamide C10H16N2O2S 详情 详情
(IX) 12403 N-[4-(2-[Methyl[2-(4-nitrophenoxy)ethyl]amino]ethyl)phenyl]methanesulfonamide C18H23N3O5S 详情 详情
(X) 12404 N-(4-[2-[[2-(4-Aminophenoxy)ethyl](methyl)amino]ethyl]phenyl)methanesulfonamide C18H25N3O3S 详情 详情
(XI) 12405 4-[(methylsulfonyl)amino]phenethyl methanesulfonate C10H15NO5S2 详情 详情
(XII) 12406 N-[4-[2-(Methylamino)ethoxy]phenyl]methanesulfonamide C10H16N2O3S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

 

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) 12395 N-Methyl-N-(4-nitrophenethyl)amine; N-Methyl-2-(4-nitrophenyl)-1-ethanamine C9H12N2O2 详情 详情
(VI) 12400 N-(4-[2-[Methyl(4-nitrophenethyl)amino]ethoxy]phenyl)methanesulfonamide C18H23N3O5S 详情 详情
(VII) 12401 N-(4-[2-[(4-Aminophenethyl)(methyl)amino]ethoxy]phenyl)methanesulfonamide C18H25N3O3S 详情 详情
(XIII) 66267 N-(4-(2-bromoethoxy)phenyl)methanesulfonamide   C9H12BrNO3S 详情 详情

合成路线3

该中间体在本合成路线中的序号:(I)

 

1 Arrowsmith JE,Cross PE,et al.1987.Processes for the preparation of N-substituted p-aminoethylsufonanilides for use as antiarryhythmic agents. EP245997
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) 12395 N-Methyl-N-(4-nitrophenethyl)amine; N-Methyl-2-(4-nitrophenyl)-1-ethanamine C9H12N2O2 详情 详情
(III) 12397 N-Methyl-N-(4-nitrophenethyl)-2-(4-nitrophenoxy)-1-ethanamine; N-Methyl-N-(4-nitrophenethyl)-N-[2-(4-nitrophenoxy)ethyl]amine C17H19N3O5 详情 详情
(IV) 12398 N-(4-Aminophenethyl)-N-[2-(4-aminophenoxy)ethyl]-N-methylamine; 4-[2-[(4-Aminophenethyl)(methyl)amino]ethoxy]aniline C17H23N3O 详情 详情
(XVII) 63398 1-[(2-bromoethyl)oxy]-4-nitrobenzene; 2-bromoethyl 4-nitrophenyl ether 13288-06-7 C8H8BrNO3 详情 详情
Extended Information