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

Base Information

• Chemical Name: 1,2,3,4-Tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline
• CAS No.: 20412-65-1
• Molecular Formula: C₂₁H₂₇NO₄
• Molecular Weight: 357.45
• Mol file: 20412-65-1.mol

Synonyms:Veraisoquin;1,2,3,4-Tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline;Isoquinoline,1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl;1,2,3,4-Tetrahydro-6,7-dimethoxy-1-(3,4-dimethoxybenzyl)-2-methylisoquinoline;1-(3,4-Dimethoxybenzyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl;

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

Chemical Property:

• Vapor Pressure: 6.19E-09mmHg at 25°C
• Boiling Point: 468.1°Cat760mmHg
• Flash Point: 131.2°C
• PSA: 40.16000
• Density: 1.111g/cm³
• LogP: 3.43060

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 178 articles about 1,2,3,4-Tetrahydro-1-(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: 91.0%

(+/-)-1-(3,4-dimethoxybenzyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline (50461-24-0) → laudanosine (1699-51-0,20412-65-1)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1016/j.tetlet.2007.09.073

Reference yield: 89.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + Tetrahydropapaverine (13074-31-2) → laudanosine (1699-51-0,20412-65-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; water; Ambient temperature; 1) 1 h 2) 18 h;

DOI:10.1002/jhet.5570280720

Reference yield: 88.0%

4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) + 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile (51714-24-0) → laudanosine (1699-51-0,20412-65-1)

Guidance literature:

6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile; With potassium hexamethylsilazane; In tetrahydrofuran; at 0 ℃; for 0.25h; Inert atmosphere;

4-bromomethyl-1,2-dimethoxybenzene; In tetrahydrofuran; at 0 - 20 ℃; for 6h; Inert atmosphere;

With sodium cyanoborohydride; acetic acid; In tetrahydrofuran; ethanol; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00652

upstream raw materials:

Papaverine

2-Methylpapaverinium iodide

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

4-chloromethyl-1,2-dimethoxy-benzene

Downstream raw materials:

[2-(3,4-dimethoxy-styryl)-4,5-dimethoxy-phenethyl]-dimethyl-amine

(R)-laudanosine

(+/-)-N-ethyl-Laudanosine iodide