6,7-Dimethoxy-1-phenyl-3,4-dihydroisoquinoline--hydrogen chloride (1/1)

Base Information

• Chemical Name: 6,7-Dimethoxy-1-phenyl-3,4-dihydroisoquinoline--hydrogen chloride (1/1)
• CAS No.: 10133-76-3
• Molecular Formula: C17H17NO2.ClH
• Molecular Weight: 303.788
• DSSTox Substance ID: DTXSID20496168
• Mol file: 10133-76-3.mol

Synonyms:DTXSID20496168;10133-76-3;6,7-Dimethoxy-1-phenyl-3,4-dihydroisoquinoline--hydrogen chloride (1/1)

Chemical Property of 6,7-Dimethoxy-1-phenyl-3,4-dihydroisoquinoline--hydrogen chloride (1/1)

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 303.1026065
• Heavy Atom Count: 21
• Complexity: 349

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)CCN=C2C3=CC=CC=C3)OC.Cl

Technology Process of 6,7-Dimethoxy-1-phenyl-3,4-dihydroisoquinoline--hydrogen chloride (1/1)

There total 6 articles about 6,7-Dimethoxy-1-phenyl-3,4-dihydroisoquinoline--hydrogen chloride (1/1) 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: 93.0%

6,7-dimethoxy-1-(methylsulfanyl)-3,4-dihydroisoquinoline (24456-60-8) + phenylboronic acid (98-80-6) → 3,4-dihydro-6,7-dimethoxy-1-phenylisoquinoline hydrochloride (10133-76-3)

Guidance literature:

6,7-dimethoxy-1-(methylsulfanyl)-3,4-dihydroisoquinoline; phenylboronic acid; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) thiophene-2-carboxylate; In tetrahydrofuran; Inert atmosphere; Reflux;

With hydrogenchloride;

DOI:10.1007/s00706-015-1564-y

Reference yield:

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 3,4-dihydro-6,7-dimethoxy-1-phenylisoquinoline hydrochloride (10133-76-3)

Guidance literature:

Multi-step reaction with 4 steps

1: Acidic conditions

2: sulfur / N,N-dimethyl-formamide / 0.25 h / 170 °C / Microwave irradiation

3: caesium carbonate / acetonitrile; dichloromethane / 24 h / 20 °C

4: copper(I) thiophene-2-carboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / Inert atmosphere; Reflux

With sulfur; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) thiophene-2-carboxylate; caesium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: |Pictet-Spengler Synthesis;

DOI:10.1007/s00706-015-1564-y

Reference yield:

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (1745-07-9) → 3,4-dihydro-6,7-dimethoxy-1-phenylisoquinoline hydrochloride (10133-76-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfur / N,N-dimethyl-formamide / 0.25 h / 170 °C / Microwave irradiation

2: caesium carbonate / acetonitrile; dichloromethane / 24 h / 20 °C

3: copper(I) thiophene-2-carboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / Inert atmosphere; Reflux

With sulfur; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) thiophene-2-carboxylate; caesium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1007/s00706-015-1564-y

upstream raw materials:

N-[2-(3,4-dimethoxyphenyl)ethyl]benzamide

benzoyl chloride

2-(3,4-dimethoxyphenyl)-ethylamine

6,7-dimethoxy-1-(methylsulfanyl)-3,4-dihydroisoquinoline

Downstream raw materials:

6,7-dimethoxy-2-methyl-1-phenyl-3,4-dihydroisoquinolinium iodide

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

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