1,2,3,4-tetrahydro-4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline

Base Information

• Chemical Name: 1,2,3,4-tetrahydro-4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline
• CAS No.: 74199-82-9
• Molecular Formula: C₂₁H₂₇NO₄
• Molecular Weight: 357.45
• Mol file: 74199-82-9.mol

Synonyms:1,2,3,4-tetrahydro-4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline

Chemical Property of 1,2,3,4-tetrahydro-4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,3,4-tetrahydro-4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline

There total 9 articles about 1,2,3,4-tetrahydro-4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline 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:

C21H29NO5 → 1,2,3,4-tetrahydro-4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline (74199-82-9)

Guidance literature:

C₂₁H₂₉NO₅; With thionyl chloride; In dichloromethane; for 8h;

With sodium hydroxide; In dichloromethane; water;

DOI:10.1055/s-0036-1588920

Reference yield:

4,5-dimethoxy-2-methoxycarbonylmethyl-benzoic acid methyl ester (68204-77-3) → 1,2,3,4-tetrahydro-4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline (74199-82-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C

1.2: 3 h / -78 - 25 °C

2.1: methanol; potassium hydroxide / water / 6 h / 0 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dmap / dichloromethane / 0 - 25 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 °C / Reflux

5.1: thionyl chloride / dichloromethane / 8 h

With methanol; dmap; lithium aluminium tetrahydride; thionyl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1055/s-0036-1588920

Reference yield:

3,4-dimethoxybenzyl mesylate → 1,2,3,4-tetrahydro-4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline (74199-82-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C

1.2: 3 h / -78 - 25 °C

2.1: methanol; potassium hydroxide / water / 6 h / 0 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dmap / dichloromethane / 0 - 25 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 °C / Reflux

5.1: thionyl chloride / dichloromethane / 8 h

With methanol; dmap; lithium aluminium tetrahydride; thionyl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1055/s-0036-1588920

upstream raw materials:

4,5-dimethoxy-2-methoxycarbonylmethyl-benzoic acid methyl ester

3,4-dimethoxy-benzaldehyde

Downstream raw materials:

4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-3,4-dihydroisoquinolinium trifluoroacetate

4-(3,4-dimethoxybenzylidene)-6,7-dimethoxy-2-methyl-3,4-dihydroisoquinolinium trifluoroacetate