1-(3,4-Dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride

Base Information

• Chemical Name: 1-(3,4-Dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride
• CAS No.: 5884-22-0
• Molecular Formula: C20H23 N O4 . Cl H
• Molecular Weight: 377.868
• Hs Code.: 2933499090
• European Community (EC) Number: 227-560-0
• DSSTox Substance ID: DTXSID30974346
• NSC Number: 118078
• Mol file: 5884-22-0.mol

Synonyms:1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride;3,4-dihydropapaverine;3,4-dihydropapaverine, monohydrobromide;3,4-dihydropapaverine, monohydrochloride

Chemical Property of 1-(3,4-Dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride

Chemical Property:

• Vapor Pressure: 5.28E-09mmHg at 25°C
• Melting Point: 202ºC
• Boiling Point: 482.6°Cat760mmHg
• Flash Point: 196.9°C
• PSA: 49.28000
• Density: g/cm³
• LogP: 3.54650
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 377.1393859
• Heavy Atom Count: 26
• Complexity: 455

Purity/Quality:

99% ^*data from raw suppliers

1-[(3,4-DIMETHOXYPHENYL)METHYL]-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLINE HYDROCHLORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CC2=NCCC3=CC(=C(C=C32)OC)OC)OC.Cl

Technology Process of 1-(3,4-Dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride

There total 5 articles about 1-(3,4-Dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride 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%

N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide (139-76-4) → 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride (5884-22-0)

Guidance literature:

N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide; With trichlorophosphate; In toluene; at 20 ℃; for 1h; Reflux; Inert atmosphere;

With hydrogenchloride;

DOI:10.1021/acs.joc.9b01604

Reference yield:

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) → 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride (5884-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 12 h / Reflux

2: trichlorophosphate / acetonitrile / 17 h / 20 - 80 °C

With trichlorophosphate; In toluene; acetonitrile;

Reference yield:

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride (5884-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 12 h / Reflux

2: trichlorophosphate / acetonitrile / 17 h / 20 - 80 °C

With trichlorophosphate; In toluene; acetonitrile;

upstream raw materials:

N-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dimethoxyphenylacetamide

N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide

2-(3,4-dimethoxyphenyl)-ethylamine

(3,4-Dimethoxyphenyl)acetic acid

Downstream raw materials:

2-[1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]phenyl ethyl carbonate

diethyl-carbamic acid 2-[1-(3,4-dimethoxy-phenyl)-8,9-dimethoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinolin-2-yl]-phenyl ester

2-[1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]-4,5-dimethoxyphenyl ethyl carbonate

diethyl-carbamic acid 2-[1-(3,4-dimethoxy-phenyl)-8,9-dimethoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinolin-2-yl]-4,5-dimethoxy-phenyl ester

Refernces

• 1、 Klintworth, Robin,De Koning, Charles B.,Opatz, Till,Michael, Joseph P.. "A xylochemically inspired synthesis of lamellarin G trimethyl ether via an enaminone intermediate". . p. 11025 - 11031. Retrieved 2019/09/12.
• 2、 Yamamoto, Yasutomo,Tabuchi, Yuri,Baba, Ayana,Hideshima, Kumiko,Nakano, Mai,Miyawaki, Akari,Tomioka, Kiyoshi. "Total synthesis of 8-epi-javaberine A and javaberine A". . p. 1311 - 1321. Retrieved 2016/11/07.