6-o-Desmethyldonepezil

Base Information

• Chemical Name: 6-o-Desmethyldonepezil
• CAS No.: 120013-56-1
• Molecular Formula: C23H27 N O3
• Molecular Weight: 365.472
• UNII: 556XXE4I5F
• DSSTox Substance ID: DTXSID60561627
• Metabolomics Workbench ID: 42545
• Nikkaji Number: J1.010.441F
• Wikidata: Q27261288
• Mol file: 120013-56-1.mol

Synonyms:6-O-desmethyl donepezil

Chemical Property of 6-o-Desmethyldonepezil

Chemical Property:

• Melting Point: 57-59掳C
• Boiling Point: 545.3±50.0 °C(Predicted)
• PKA: 9.46±0.40(Predicted)
• PSA: 49.77000
• Density: 1.190±0.06 g/cm3(Predicted)
• LogP: 3.99600
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Dichloromethane, Methanol (Slightly)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 365.19909372
• Heavy Atom Count: 27
• Complexity: 496

Purity/Quality:

95% ^*data from raw suppliers

6-O-Desmethyl Donepezil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)CC(C2=O)CC3CCN(CC3)CC4=CC=CC=C4)O
• Uses: A metabolite of Donepezil, an inhibitor of acetylcholinesterase A metabolite of Donepezil (D531750), an inhibitor of acetylcholinesterase.

Technology Process of 6-o-Desmethyldonepezil

There total 8 articles about 6-o-Desmethyldonepezil 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: 94.0%

(E)-2-((1-benzylpiperidin-4-yl)methylene)-6-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one → O6-Demethyl-Donepezil (120013-56-1)

Guidance literature:

With methyl-phenyl-thioether; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃;

DOI:10.3390/molecules23123252

Reference yield: 94.0%

(Z)-2-((1-benzylpiperidin-4-yl)methylene)-6-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one → O6-Demethyl-Donepezil (120013-56-1)

Guidance literature:

With methyl-phenyl-thioether; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃; Sealed tube;

DOI:10.3390/molecules25010077

Reference yield: 43.0%

donepezil (120014-06-4,142057-79-2,142057-80-5,142698-19-9) → O6-Demethyl-Donepezil (120013-56-1)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide; at 60 ℃; for 5h;

upstream raw materials:

donepezil

3-(4-hydroxy-3-methoxyphenyl)propionic acid

6-hydroxy-5-methoxyindan-1-one

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Downstream raw materials:

tert-butyl 2-(2-((1-benzylpiperidin-4-yl)methyl)-6-methoxy-3-oxo-2,3-dihydro-1H-inden-5-yloxy)acetate

Refernces

• 1、 Green, Keith D.,Fosso, Marina Y.,Garneau-Tsodikova, Sylvie. "Multifunctional donepezil analogues as cholinesterase and BACE1 inhibitors". . . Retrieved 2018/12/13.