N-[(1S,2S)-2-(3,4-dichloroanilino)cyclopentyl]-N,N-dimethylamine; (1S,2S)-N(1)-(3,4-dichlorophenyl)-N(2),N(2)-dimethyl-1,2-cyclopentanediamine -Drug Synthesis Database

【结构式】

【分子编号】34277

【品名】N-[(1S,2S)-2-(3,4-dichloroanilino)cyclopentyl]-N,N-dimethylamine; (1S,2S)-N(1)-(3,4-dichlorophenyl)-N(2),N(2)-dimethyl-1,2-cyclopentanediamine

【CA登记号】

【分子式】C₁₃H₁₈Cl₂N₂

【分子量】273.2048

【元素组成】C 57.15% H 6.64% Cl 25.95% N 10.25%

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：(VI)

The reaction of cyclopentene oxide (I) with dimethylamine (II) gives 2-(dimethylamino)cyclopentanol (III), which is treated with methanesulfonyl chloride and NaH in THF to afford the corresponding methasulfonyl ester (IV). The condensation of (IV) with 3,4-dichloroaniline (V) in THF yields N,N-dimethyl-N'-(3,4-dichlorophenyl)cyclopentane-1,2-diamine (VI), which is acylated with propionic anhydride (A) and treated finally with maleic acid (B).

参考文献中间体

合成目标

【1】 Szmuszkovicz, J.; N-(2-Aminocyclopentyl)acylanilides and treating depression. BE 0861351; BE 0861355; US 4156015 .
【2】 Szmuszkovicz, J.; Composes alcanoylanilides et leur preparation. BE 0875461 .
【3】 Szmuszkovicz, J.; N-(2-aminocyclopentyl)amides. BE 0867554; DE 2817112; FR 2416882; GB 1581914; JP 54106451; NL 7803442 .
【4】 Szmuszkovicz, J.; Anilide derivatives as antidepressants. US 4128663; US 4148913 .
【5】 Szmuszkovicz, J.; N-(2-Aminocyclopentyl)acylanilides and treating depression. US 4156733; US 4157398 .
【6】 Szmuszkovicz, J.; Kane, M.P.; von Voigtlander, P.F.; A new non-tricyclic antidepressant agent. Synthesis and activity of N-[trans-2-(dimethyamino)cyclopentyl]-N-(3,4-dichlorophenyl)propanamide and related compounds. J Med Chem 1981, 24, 10, 1230-36.
【7】 Owen, R.T.; Serradell, M.N.; Castaner, J.; U-48753 E. Drugs Fut 1984, 9, 11, 846.

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)	20095	propionic anhydride	123-62-6	C₆H₁₀O₃	详情	详情
(B)	23808	Fumaric acid; (E)-2-butenedioic acid	110-17-8	C₄H₄O₄	详情	详情
(I)	34274	(1R,5S)-6-oxabicyclo[3.1.0]hexane		C₅H₈O	详情	详情
(II)	19443	N-methylmethanamine; N,N-dimethylamine	124-40-3	C₂H₇N	详情	详情
(III)	34275	(1S,2S)-2-(dimethylamino)cyclopentanol		C₇H₁₅NO	详情	详情
(IV)	34276	N,N-dimethyl-N-((1S,2S)-2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]cyclopentyl)amine; (1S,2S)-N,N-dimethyl-2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]cyclopentanamine		C₁₀H₂₁NOS	详情	详情
(V)	23629	3,4-dichloroaniline	95-76-1	C₆H₅Cl₂N	详情	详情
(VI)	34277	N-[(1S,2S)-2-(3,4-dichloroanilino)cyclopentyl]-N,N-dimethylamine; (1S,2S)-N(1)-(3,4-dichlorophenyl)-N(2),N(2)-dimethyl-1,2-cyclopentanediamine		C₁₃H₁₈Cl₂N₂	详情	详情

Extended Information