6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

Base Information

Chemical Name:6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline
CAS No.:573674-56-3
Molecular Formula:C₃₀H₃₆N₂O₃
Molecular Weight:472.627
Hs Code.:

Synonyms:6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

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Chemical Property of 6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

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Technology Process of 6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

There total 7 articles about 6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

: 7250-67-1
1-(2-chloroethyl)pyrrolidine hydrochloride

: 573674-55-2
4-[6-methoxy-2-(3-methoxyphenyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]phenol

: 573674-56-3
6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: 4-[6-methoxy-2-(3-methoxyphenyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]phenol; With sodium hydride; In 1,4-dioxane; at 20 ℃; for 0.166667h;

1-(2-chloroethyl)pyrrolidine hydrochloride; With sodium hydride; In 1,4-dioxane; at 80 ℃; for 17.5h;
DOI:10.1021/jm030086h

Reference yield:

: 2398-37-0
3-methoxyphenyl bromide

: 573674-56-3
6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / CuI; K₂CO₃ / dimethylformamide / 118 h / 150 °C

2.1: hexane; tetrahydrofuran / 0.75 h / -78 °C

2.2: aq. HClO₄ / hexane; tetrahydrofuran; ethyl acetate / 0.17 h

3.1: 4.74 g / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C

4.1: 66 percent / AlCl₃; Me₂NPh / CH₂Cl₂ / 1 h / 20 °C

5.1: NaH / dioxane / 0.17 h / 20 °C

5.2: 100 percent / NaH / dioxane / 17.5 h / 80 °C

With copper(l) iodide; aluminium trichloride; sodium hydride; potassium carbonate; N,N-dimethyl-aniline; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Ullmann reaction;
DOI:10.1021/jm030086h

Reference yield:

: 4-Benzyloxyphenyl lithium

: 573674-56-3
6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 4 steps

1.1: hexane; tetrahydrofuran / 0.75 h / -78 °C

1.2: aq. HClO₄ / hexane; tetrahydrofuran; ethyl acetate / 0.17 h

2.1: 4.74 g / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C

3.1: 66 percent / AlCl₃; Me₂NPh / CH₂Cl₂ / 1 h / 20 °C

4.1: NaH / dioxane / 0.17 h / 20 °C

4.2: 100 percent / NaH / dioxane / 17.5 h / 80 °C

With aluminium trichloride; sodium hydride; N,N-dimethyl-aniline; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane;
DOI:10.1021/jm030086h