Tetrahydropapaveroline hydrochloride

Base Information

• Chemical Name: Tetrahydropapaveroline hydrochloride
• CAS No.: 3184-36-9
• Molecular Formula: C16H17 N O4 . Cl H
• Molecular Weight: 323.776
• European Community (EC) Number: 221-680-7
• UNII: NF7L11I15K
• DSSTox Substance ID: DTXSID50953754
• Wikidata: Q27284842
• Mol file: 3184-36-9.mol

Synonyms:Tetrahydropapaveroline hydrochloride;3184-36-9;THP hydrochloride;UNII-NF7L11I15K;NF7L11I15K;6,7-Isoquinolinediol, 1-((3,4-dihydroxyphenyl)methyl)-1,2,3,4-tetrahydro-, hydrochloride;6,7-Isoquinolinediol, 1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-, hydrochloride;DTXSID50953754;1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium-6,7-diol chloride;DL-TETRAHYDROPAPAVEROLINE HYDROCHLORIDE;Q27284842;TETRAHYDROPAPAVEROLINE HYDROCHLORIDE, (+/-)-;TETRAHYDROPAPAVEROLINE (+/-)-FORM HYDROCHLORIDE [MI];1-((3,4-DIHYDROXYPHENYL)METHYL)-1,2,3,4-TETRAHYDRO-6,7-ISOQUINOLINEDIOL HYDROCHLORIDE;1-[(3,4-Dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol--hydrogen chloride (1/1);6,7-ISOQUINOLINEDIOL, 1-((3,4-DIHYDROXYPHENYL)METHYL)-1,2,3,4-TETRAHYDRO-, HYDROCHLORIDE (1:1)

Chemical Property of Tetrahydropapaveroline hydrochloride

Chemical Property:

• Vapor Pressure: 9.67E-14mmHg at 25°C
• Melting Point: 291-293 °C
• Boiling Point: 573.2°Cat760mmHg
• Flash Point: 235.1°C
• PSA: 92.95000
• Density: g/cm³
• LogP: 3.06930
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 323.0924357
• Heavy Atom Count: 22
• Complexity: 353

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC(=C(C=C3)O)O.Cl

Technology Process of Tetrahydropapaveroline hydrochloride

There total 10 articles about Tetrahydropapaveroline hydrochloride 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: 81.0%

6,7-bisbenzyloxy-1-(3,4-bisbenzyloxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (79832-14-7) → norlaudanosoline hydrochloride (3184-36-9)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; for 2h;

DOI:10.1039/P19810002016

Reference yield:

3,4-bis(benzyloxy)-β-nitrostyrene (1699-54-3) → norlaudanosoline hydrochloride (3184-36-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / lithium aluminium hydride / tetrahydrofuran / 1.25 h / Heating

2: sodium hydrogen carbonate / CH₂Cl₂; H₂O / 1.5 h

3: 85 percent / phosphorus oxychloride / acetonitrile / 0.42 h / Heating

4: 92 percent / sodium borohydride / methanol / 0.75 h / 0 °C

5: 81 percent / hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; sodium hydrogencarbonate; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1039/P19810002016

Reference yield:

(3,4-bis-benzyloxyphenyl)acetonitrile (1699-60-1) → norlaudanosoline hydrochloride (3184-36-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / potassium hydroxide, water / ethane-1,2-diol / 18 h / Heating

2: oxalyl chloride, DMF / benzene / 1 h / 20 °C

3: sodium hydrogen carbonate / CH₂Cl₂; H₂O / 1.5 h

4: 85 percent / phosphorus oxychloride / acetonitrile / 0.42 h / Heating

5: 92 percent / sodium borohydride / methanol / 0.75 h / 0 °C

6: 81 percent / hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; oxalyl dichloride; water; hydrogen; sodium hydrogencarbonate; N,N-dimethyl-formamide; trichlorophosphate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; ethylene glycol; acetonitrile; benzene;

DOI:10.1039/P19810002016

upstream raw materials:

6,7-bisbenzyloxy-1-(3,4-bisbenzyloxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride

3,4-bis(benzyloxy)-β-nitrostyrene

(3,4-bis-benzyloxyphenyl)acetonitrile

<3,4-bis(benzyloxy)phenyl>acetic acid

Refernces

• 1、 Brochmann-Hanssen,Chen,Chiang,Fu,Nemoto. "Opium alkaloids. XIV: Biosynthesis of aporphines: Detection of orientaline in opium poppy". . p. 1291 - 1293. Retrieved 2007/10/05.