pentamethylene bis[1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate], dioxalate

Base Information

• Chemical Name: pentamethylene bis[1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate], dioxalate
• CAS No.: 64228-78-0
• Molecular Formula: 2C₂H₂O₄*C₅₁H₆₆N₂O₁₂
• Molecular Weight: 1079.16
• Hs Code.: 2933499090
• European Community (EC) Number: 264-741-3
• DSSTox Substance ID: DTXSID30867062
• Mol file: 64228-78-0.mol

Synonyms:64228-78-0;EINECS 264-741-3;pentamethylene bis[1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate], dioxalate;CisAtracurium Oxalate;5-[3-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]propanoyloxy]pentyl 3-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]propanoate;oxalic acid;Atracurium dioxalate;Pentamethylene bis(1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate), dioxalate;Atracuriumdioxalate;DTXSID30867062;BCP22907;AKOS015951366;C51H66N2O12.2C2H2O4;AC-24188;AS-75189;Pentamethylene bis[1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate] dioxalate;FT-0655115;FT-0694090;C51-H66-N2-O12.2C2-H2-O4;B0371-336184;5-[(3-{1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl}propanoyl)oxy]pentyl 3-{1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl}propanoate;bis(oxalic acid);cis-Atracurium oxalate pound>>Atracurium Besylate EP impurity B;(R,R)-N,N inverted exclamation mark -Didemethyl Atracurium Oxalate;Pentane-1,5-diyl bis(3-(1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)propanoate) dioxalate

Chemical Property of pentamethylene bis[1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate], dioxalate

Chemical Property:

• Vapor Pressure: 1.44E-34mmHg at 25°C
• Boiling Point: 916.8 °C at 760 mmHg
• Flash Point: 508.3 °C
• PSA: 206.70000
• LogP: 4.46930
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 22
• Rotatable Bond Count: 28
• Exact Mass: 1078.45219263
• Heavy Atom Count: 77
• Complexity: 1370

Purity/Quality:

98%min. ^*data from raw suppliers

Atracuriumdioxalate 97% ^*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)CC2C3=CC(=C(C=C3CCN2CCC(=O)OCCCCCOC(=O)CCN4CCC5=CC(=C(C=C5C4CC6=CC(=C(C=C6)OC)OC)OC)OC)OC)OC)OC.C(=O)(C(=O)O)O.C(=O)(C(=O)O)O

Technology Process of pentamethylene bis[1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate], dioxalate

There total 10 articles about pentamethylene bis[1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate], dioxalate 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: 86.0%

1 ,5-pentanediol (111-29-5) + (1R)-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-tert-butoxycarbonylethyl-isoquinoline oxalate (1075726-71-4) + oxalic acid (144-62-7,97993-78-7) → N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine dioxalate (64228-78-0,64493-10-3,83285-74-9,96687-52-4,96687-53-5,110817-20-4)

Guidance literature:

(1R)-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-tert-butoxycarbonylethyl-isoquinoline oxalate; With ammonium hydroxide; In water; for 0.5h;

With toluene-4-sulfonic acid; at 50 - 55 ℃; for 4.5h;

1 ,5-pentanediol; oxalic acid; Further stages;

Reference yield: 51.0%

pentamethylene 1,5-diacrylate (36840-85-4) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5,66820-84-6) → pentamethylene bis(1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate) dioxalate (64228-78-0,64493-10-3,83285-74-9,96687-52-4,96687-53-5,110817-20-4)

Guidance literature:

In benzene; for 48h; Heating;

Reference yield:

pentamethylene 1,5-diacrylate (36840-85-4) + (R)-tetrahydropapaverine-N-acetyl-D-leucine salt (876290-45-8,141109-12-8) + oxalic acid (144-62-7,97993-78-7) + acetic anhydride (108-24-7) → N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine dioxalate (64228-78-0,64493-10-3,83285-74-9,96687-52-4,96687-53-5,110817-20-4) + (R)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (860-24-2,860-23-1)

Guidance literature:

(R)-tetrahydropapaverine-N-acetyl-D-leucine salt; With ammonia; In dichloromethane; water;

pentamethylene 1,5-diacrylate; With acetic acid; at 70 - 75 ℃; Inert atmosphere;

oxalic acid; acetic anhydride;

upstream raw materials:

pentamethylene 1,5-diacrylate

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride

(3,4-Dimethoxyphenyl)acetic acid

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

Downstream raw materials:

C₅₃H₇₂N₂O₁₂⁽²⁺⁾*2C₇H₇O₃S^(1-)

cisatracurium besylate

C₅₀H₆₆N₂O₁₂⁽²⁺⁾*2CH₃O₃S^(1-)

C₅₃H₇₂N₂O₁₂⁽²⁺⁾*2I^(1-)

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF TETRAHYDROISOQUINOLINE COMPOUNDS". Page/Page column 25. . Retrieved 2018/11/22.
• 2、 Stenlake,Waigh,Dewar,et al.. "Biodegradable neuromuscular blocking agents. Part 4. Atracurium besylate and related polyalkylene di-esters". . p. 515 - 524. Retrieved 2007/10/02.