1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol -Drug Synthesis Database

【结构式】

【分子编号】23244

【品名】1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol

【CA登记号】93413-77-5

【分子式】C₁₅H₂₃NO₂

【分子量】249.35316

【元素组成】C 72.25% H 9.3% N 5.62% O 12.83%

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：(IV)

The condensation of cyclohexanone (I) with 4 methoxyphenylacetonitrile (II) by means of n-butyllithium in THF gives 2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl) acetonitrile (III), which is reduced with H2 over Rh/A12O3 in ethanol-ammonia yielding 1-[2-amino-1-(4 methoxyphenyl)ethyl]cyclohexanol (IV). Finally, this compound is methylated with formaldehyde and formic acid in refluxing water.

参考文献中间体

合成目标

【1】 Husbands, G.E.; et al.; Novel phenethylamine antidepressants. 190th ACS Natl Meet (Chicago) 1985, 20, 29-30, Abst MEDI 80.
【2】 Morris, G.E.; Muth, E.A.; Yardley, J.P. (American Home Products Corp.); Phenethylamine derivs.. EP 0112669; ES 8702336; GB 2133788; JP 1991135948; JP 1991178953; US 4535186 .
【3】 Prous, J.; Castaner, J.; WY-45030. Drugs Fut 1988, 13, 9, 839.
【4】 Yardley, J.P.; Husbands, G.E.M.; Stack, G.; et al.; 2-Phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives: Synthesis and antidepressant activity. J Med Chem 1990, 33, 10, 2899-905.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	11059	Cyclohexanone	108-94-1	C₆H₁₀O	详情	详情
(II)	23242	2-(4-methoxyphenyl)acetonitrile; 4-methoxybenzeneacetonitrile	104-47-2	C₉H₉NO	详情	详情
(III)	23243	2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)acetonitrile		C₁₅H₁₉NO₂	详情	详情
(IV)	23244	1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol	93413-77-5	C₁₅H₂₃NO₂	详情	详情

Extended Information