2-(methylamino)-1-phenyl-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】62404

【品名】2-(methylamino)-1-phenyl-1-ethanol

【CA登记号】

【分子式】C₉H₁₃NO

【分子量】151.20836

【元素组成】C 71.49% H 8.67% N 9.26% O 10.58%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XVI)

In a different method, reaction of styrene oxide (XV) with methylamine provided amino alcohol (XVI), which was further condensed with ethylene oxide (XVII) to afford amino diol (XVIII). Alternatively, diol (XVIII) was prepared by a more direct procedure by condensation of epoxide (XV) with 2-(methylamino)ethanol (XIX). Chlorination of (XVIII) employing SOCl2 yielded the dichloro derivative (XX), which was subsequently condensed with 2-aminobenzyl alcohol (X) leading to piperazine (XXI). Cyclization of (XXI) to the title compound was accomplished by treatment with hot polyphosphoric acid. Optionally, alcohol (XXI) was converted to chloride (XXII), which was then cyclized in the presence of AlCl3. In a related method, alcohol (XXI) was esterified with AcOH, and the resultant acetate ester (XXIII) was then cyclized in the presence of polyphosphoric acid

参考文献中间体

合成目标

【1】 Olivié, J.; Synthesis for the preparation of tetracyclic cpds.. US 4217452 .

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
(XVI)	62404	2-(methylamino)-1-phenyl-1-ethanol		C₉H₁₃NO	详情	详情
(XVII)	10393	Oxirane; Ethylene oxide	75-21-8	C₂H₄O	详情	详情
(XVIII)	62405	2-[(2-hydroxyethyl)(methyl)amino]-1-phenyl-1-ethanol		C₁₁H₁₇NO₂	详情	详情
(XIX)	13324	2-Methylaminoethanol; 2-(Methylamino)-1-ethanol	109-83-1	C₃H₉NO	详情	详情
(XX)	62406	2-chloro-N-(2-chloroethyl)-N-methyl-2-phenyl-1-ethanamine; N-(2-chloroethyl)-N-(2-chloro-2-phenylethyl)-N-methylamine		C₁₁H₁₅Cl₂N	详情	详情
(XXI)	62407	[2-(4-methyl-2-phenyl-1-piperazinyl)phenyl]methanol		C₁₈H₂₂N₂O	详情	详情
(XXII)	62408	1-[2-(chloromethyl)phenyl]-4-methyl-2-phenylpiperazine		C₁₈H₂₁ClN₂	详情	详情
(XXIII)	62409	2-(4-methyl-2-phenyl-1-piperazinyl)benzyl acetate		C₂₀H₂₄N₂O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVI)

The key intermediate (XXI) was also prepared by several related procedures. Chlorination of aminoalcohol (XVI) gave chloro amine (XXIV), which was condensed with 2-aminobenzyl alcohol (X) to afford diamine (XXV). Then, alkylation of diamine (XXV) with dibromoethane (XIII) in hot pyridine gave rise to the target piperazine (XXI). Alternatively, diamine (XXV) was condensed with ethyl chloroacetate or with diethyl oxalate to produce the mono- or dioxopiperazines (XXVII) and (XXVI), respectively, which were then reduced to (XXI) by means of LiAlH4. Cyclization of alcohol (XXI) to the title compound was achieved by treatment with concentrated sulfuric acid

参考文献中间体

合成目标

【1】 Olivié, J.; Synthesis for the preparation of tetracyclic cpds.. US 4217452 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	16601	ethyl chloroacetate; ethyl 2-chloroacetate	105-39-5	C₄H₇ClO₂	详情	详情
(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
(XIII)	10252	1,2-Dibromoethane; Ethylene dibromide	106-93-4	C₂H₄Br₂	详情	详情
(XVI)	62404	2-(methylamino)-1-phenyl-1-ethanol		C₉H₁₃NO	详情	详情
(XXI)	62407	[2-(4-methyl-2-phenyl-1-piperazinyl)phenyl]methanol		C₁₈H₂₂N₂O	详情	详情
(XXIV)	62410			C₁₀H₁₆ClN	详情	详情
(XXV)	62411	(2-{[2-(methylamino)-1-phenylethyl]amino}phenyl)methanol		C₁₆H₂₀N₂O	详情	详情
(XXVI)	62413	4-[2-(hydroxymethyl)phenyl]-1-methyl-5-phenyl-2,3-piperazinedione		C₁₈H₁₈N₂O₃	详情	详情
(XXVII)	62412	1-[2-(hydroxymethyl)phenyl]-4-methyl-6-phenyl-2-piperazinone		C₁₈H₂₀N₂O₂	详情	详情

Extended Information