4-[(S)-[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide -Drug Synthesis Database

【结构式】

【分子编号】56250

【品名】4-[(S)-[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide

【CA登记号】

【分子式】C₂₈H₃₉N₃O₂

【分子量】449.63668

【元素组成】C 74.8% H 8.74% N 9.35% O 7.12%

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：(X)

The alkylation of trans-2,5-dimethylpiperazine (VIII) with allyl bromide gave rise to a racemic mixture of N-allylpiperazines, which was resolved using (-)-camphoric acid. The desired (2R,5S)-piperazine (IX) was then alkylated with benzhydryl chloride (VII) producing a mixture of the title compound and its benzhydryl epimer (X), which were separated by flash column chromatography.

参考文献中间体

合成目标

【1】 Evans, S.M.; Lenz, G.R.; Probes of receptor mediated phenomena 19. Synthesis of (+)-4-[(alphaR)-alpha((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide (SNC 80): A highly selective, nonpeptide delta opioid receptor agonist. Chemtracts - Org Chem 1994, 7, 6, 395.
【2】 Calderon, S.N.; et al.; Probes for narcotic receptor mediated phenomena: 23. Synthesis, opioid receptor binding, and bioassay of the highly selective delta agonist (+)-4-[(alphaR)-alpha-((2S,5R)-4-allyl-2, 5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N, N-diethylbenzamide (SNC 80). J Med Chem 1997, 40, 5, 695.
【3】 Calderon, S.N.; et al.; Probes for narcotic receptor mediated phenomena. 19. Synthesis of (+)-4-[(alphaR)-alpha-((2S,5R)-4-allyl-2, 5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N, N-diethylbenzamide (SNC 80): A highly selective, nonpeptide delta opioid receptor agonist. J Med Chem 1994, 14, 37, 2125.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VII)	56249	4-[chloro(3-methoxyphenyl)methyl]-N,N-diethylbenzamide	C₁₉H₂₂ClNO₂	详情	详情
(VIII)	20687	(2R,5S)-2,5-dimethylpiperazine	C₆H₁₄N₂	详情	详情
(IX)	20690	(2R,5S)-1-allyl-2,5-dimethylpiperazine	C₉H₁₈N₂	详情	详情
(X)	56250	4-[(S)-[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide	C₂₈H₃₉N₃O₂	详情	详情

Extended Information