1-[(2R)-2-chloropropyl]benzene -Drug Synthesis Database

【结构式】

【分子编号】33324

【品名】1-[(2R)-2-chloropropyl]benzene

【CA登记号】

【分子式】C₉H₁₁Cl

【分子量】154.63904

【元素组成】C 69.9% H 7.17% Cl 22.93%

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：(III)

Compound can be prepared in several related ways: 1) The condensation of N-(1-phenylisopropyl)methylamine (I) with 1,2-dibromopropene (A) by heating at 100 C gives N-(1-phenylisopropyl)-N-methyl-2-bromopropenylamine (II), which is then dehydrobrominated and isomerized by treating with KOH in refluxing ethanol water. 2) By heating a mixture of (I) and propargyl bromide (B) at 100 C. 3) By reductocondensation of (I) with propargyl aldehyde (C) by means of amalgamated Al in ethanol. 4) By condensation of (I) with formaldehyde and acetylene by means of CuCl in hot dioxane. 5) By condensation of 1-phenylisopropyl chloride (III) with N-methylpropargylamine (IV) by heating at 80 C in a sealed tube.

参考文献中间体

合成目标

【1】 Ecsery, Z.; et al.; AT 252901 .
【2】 Ecsery, Z.; et al.; AT 251560 .
【3】 Ecsery, Z.; et al.; Verfahren zur Herstellung von Phenylisopropylaminen. DE 1568277; NL 6605956 .
【4】 Ecsery, Z.; et al.; Verfahren zur Herstellung von Phenylisopropylaminen. CH 530953; DE 1227447 .
【5】 Roberts, P.J.; Castaner, J.; Selegiline. Drugs Fut 1979, 4, 2, 128.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	23634	acetylene	74-86-2	C₂H₂	详情	详情
(B)	11176	3-Bromopropyne; 3-Bromo-1-propyne	106-96-7	C₃H₃Br	详情	详情
(A)	33322	(E)-1,2-dibromo-1-propene	26391-16-2	C₃H₄Br₂	详情	详情
(I)	33321	N-methyl-N-[(1R)-1-methyl-2-phenylethyl]amine; (2R)-N-methyl-1-phenyl-2-propanamine	537-46-2	C₁₀H₁₅N	详情	详情
(II)	33323	N-[(E)-3-bromo-2-butenyl]-N-methyl-N-[(1R)-1-methyl-2-phenylethyl]amine; (E)-3-bromo-N-methyl-N-[(1R)-1-methyl-2-phenylethyl]-2-buten-1-amine		C₁₄H₂₀BrN	详情	详情
(III)	33324	1-[(2R)-2-chloropropyl]benzene		C₉H₁₁Cl	详情	详情
(IV)	33325	N-methyl-2-propyn-1-amine; N-methyl-N-(2-propynyl)amine		C₄H₇N	详情	详情
(C)	23544	propiolaldehyde		C₃H₂O	详情	详情

Extended Information