(-)-N-acetyl-6-(4-chlorobutoxy)-4-<3-(4-chlorobutoxy)phenyl>-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: (-)-N-acetyl-6-(4-chlorobutoxy)-4-<3-(4-chlorobutoxy)phenyl>-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 112896-01-2
• Molecular Formula: C₂₅H₃₁Cl₂NO₃
• Molecular Weight: 464.432
• Mol file: 112896-01-2.mol

Synonyms:(-)-N-acetyl-6-(4-chlorobutoxy)-4-<3-(4-chlorobutoxy)phenyl>-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (-)-N-acetyl-6-(4-chlorobutoxy)-4-<3-(4-chlorobutoxy)phenyl>-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-N-acetyl-6-(4-chlorobutoxy)-4-<3-(4-chlorobutoxy)phenyl>-1,2,3,4-tetrahydroisoquinoline

There total 30 articles about (-)-N-acetyl-6-(4-chlorobutoxy)-4-<3-(4-chlorobutoxy)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: 65.0%

(-)-N-acetyl-6-hydroxy-4-(3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline (112896-00-1) + 1,4-dichlorobutane (110-56-5) → (-)-N-acetyl-6-(4-chlorobutoxy)-4-<3-(4-chlorobutoxy)phenyl>-1,2,3,4-tetrahydroisoquinoline (112896-01-2)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 24h;

DOI:10.1021/ja00214a004

Reference yield: 57.0%

1-[(R)-6-Hydroxy-4-(3-hydroxy-phenyl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone (112896-00-1) + 1,4-dichlorobutane (110-56-5) → 1-{6-(4-Chloro-butoxy)-4-[3-(4-chloro-butoxy)-phenyl]-3,4-dihydro-1H-isoquinolin-2-yl}-ethanone (112896-01-2)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)95436-4

Reference yield:

3-methoxyphenyl bromide (2398-37-0) → (-)-N-acetyl-6-(4-chlorobutoxy)-4-<3-(4-chlorobutoxy)phenyl>-1,2,3,4-tetrahydroisoquinoline (112896-01-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 62 percent / magnesium / diethyl ether / 1 h / Ambient temperature

2: 90 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / 20 °C

3: zinc iodide / CH₂Cl₂ / 24 h / 20 °C

4: 3 N HCl / tetrahydrofuran / 1 h / Heating

5: 84 percent / phosphorus pentachloride / benzene / 12 h / 20 °C

6: 77 percent / tributyltin hydride, azobis(isobutyronitrile) / benzene / 4 h / Heating

7: 1.) 1 M boran 2.) HCl / 1.) tetrahydrofuran, reflux, 16 h; 0 deg C, etanol 2.) THF, 20 deg C, 20 min

8: 82 percent / triethylamine / CH₂Cl₂ / 3 h

9: 76 percent / 2 N NaOH / dioxane / 72 h / 20 °C

10: 95 percent / p-toluenesulfonic acid / benzene / 1 h / Heating

11: 97 percent / trifluoroacetic acid / CH₂Cl₂ / 0.17 h / 20 °C

12: 82 percent / sodium acetate / 16 h / 20 °C

13: 83 percent / boron tribromide / CH₂Cl₂ / 24 h / 20 °C

14: 65 percent / cesium carbonate / dimethylformamide / 24 h / 80 °C

With hydrogenchloride; sodium hydroxide; 2,2'-azobis(isobutyronitrile); phosphorus pentachloride; borane; tri-n-butyl-tin hydride; sodium acetate; boron tribromide; caesium carbonate; magnesium; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; zinc(II) iodide; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00214a004

upstream raw materials:

1-[(R)-6-Hydroxy-4-(3-hydroxy-phenyl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone

1,4-dichlorobutane

3-methoxyphenyl bromide

2,2-di(3-methoxyphenyl)acetonitrile

Refernces

• 1、 Dharanipragada,Diederich. "Diastereomeric complex formation between a novel optically active host and naproxen in aqueous solution". . p. 2443 - 2446. Retrieved 2007/10/02.