N-benzyl-2-chloro-N-(2-chloroethyl)-2-phenyl-1-ethanamine; N-benzyl-N-(2-chloroethyl)-N-(2-chloro-2-phenylethyl)amine -Drug Synthesis Database

【结构式】

【分子编号】62415

【品名】N-benzyl-2-chloro-N-(2-chloroethyl)-2-phenyl-1-ethanamine; N-benzyl-N-(2-chloroethyl)-N-(2-chloro-2-phenylethyl)amine

【CA登记号】

【分子式】C₁₇H₁₉Cl₂N

【分子量】308.25

【元素组成】C 66.24% H 6.21% Cl 23% N 4.54%

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：(XXX)

In a further procedure, styrene oxide (XV) was condensed with 2-(benzylamino)ethanol (XXVIII) to give amino diol (XXIX). After chlorination of (XXIX) using SOCl2 and DMAP, dichloro derivative (XXX) was condensed with 2-aminobenzyl alcohol (X) yielding piperazine (XXXI). Cyclization of (XXXI) in hot sulfuric acid afforded the tetracyclic compound (XXXII). The N-benzyl group of (XXXII) was then removed by treatment with butyl chloroformate producing carbamate (XXXIII), which was further hydrolyzed and decarboxylated to (XXXIV) under basic conditions. Finally, methylation of the secondary amine (XXXIV) was performed by reductive alkylation with formaldehyde either in the presence of formic acid under Leuckart-Wallach conditions or by catalytic hydrogenation

参考文献中间体

合成目标

【1】 Grafe, I.; Ahrens, K.-H.; Morsdorf, J.P.; Kisielowski-Ruppert, L. (Heumann Pharma GmbH); Process for the preparation of 1,2,3,4,10,14b-hexahydro-2-methyldibenzo[c,f]pyrazino[1,2-a]azepin and their salts. DE 4305659; EP 0612745 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	18619	(2-aminophenyl)methanol; 2-Amino-benzenemethanol；2-Hydroxymethyl aniline;2-aminobenzyl alcohol;o-Aminobenzyl 2-aminobenzylalcohol;alcohol; 2-aminobenzenemethanol; 2-aminobenzyl alcohol	5344-90-1	C₇H₉NO	详情	详情
(XV)	23017	2-phenyloxirane	96-09-3	C₈H₈O	详情	详情
(XXVIII)	25630	2-(benzylamino)-1-ethanol	104-63-2	C₉H₁₃NO	详情	详情
(XXIX)	62414	2-[benzyl(2-hydroxyethyl)amino]-1-phenyl-1-ethanol		C₁₇H₂₁NO₂	详情	详情
(XXX)	62415	N-benzyl-2-chloro-N-(2-chloroethyl)-2-phenyl-1-ethanamine; N-benzyl-N-(2-chloroethyl)-N-(2-chloro-2-phenylethyl)amine		C₁₇H₁₉Cl₂N	详情	详情
(XXXI)	62416	[2-(4-benzyl-2-phenyl-1-piperazinyl)phenyl]methanol		C₂₄H₂₆N₂O	详情	详情
(XXXII)	62417	2-benzyl-1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine		C₂₄H₂₄N₂	详情	详情
(XXXIII)	62418	butyl 3,4,10,14b-tetrahydrodibenzo[c,f]pyrazino[1,2-a]azepine-2(1H)-carboxylate		C₂₂H₂₆N₂O₂	详情	详情
(XXXIV)	62419	1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine		C₁₇H₁₈N₂	详情	详情

Extended Information