Donepezil

Base Information

• Chemical Name: Donepezil
• CAS No.: 120014-06-4
• Molecular Formula: C24H29NO3
• Molecular Weight: 379.499
• Hs Code.: 29333990
• European Community (EC) Number: 601-651-9
• UNII: 8SSC91326P
• DSSTox Substance ID: DTXSID8048317
• Nikkaji Number: J458.527E
• Wikipedia: Donepezil
• Wikidata: Q415081
• NCI Thesaurus Code: C66874
• RXCUI: 135447
• Pharos Ligand ID: 32ZAJ8M5AMJT
• Metabolomics Workbench ID: 145574
• ChEMBL ID: CHEMBL502
• Mol file: 120014-06-4.mol

Synonyms:1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine hydrochloride;Aricept;donepezil;donepezil hydrochloride;donepezilium oxalate trihydrate;E 2020;E-2020;E2020;Eranz

Chemical Property of Donepezil

Chemical Property:

• Appearance/Colour: white or almost white crystal powder
• Vapor Pressure: 3.11E-11mmHg at 25°C
• Melting Point: 207 ºC
• Refractive Index: 1.578
• Boiling Point: 527.9 ºC at 760 mmHg
• PKA: 8.84±0.10(Predicted)
• Flash Point: 273.1 ºC
• PSA: 38.77000
• Density: 1.141 g/cm³
• LogP: 4.29900
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Acetone (Slightly), Chloroform (Slightly)
• Water Solubility.: 2.931 mg/L
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 379.21474379
• Heavy Atom Count: 28
• Complexity: 510

Purity/Quality:

98%, ^*data from raw suppliers

Donepezil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Alzheimer Disease Agents
• Canonical SMILES: COC1=C(C=C2C(=C1)CC(C2=O)CC3CCN(CC3)CC4=CC=CC=C4)OC
• Recent ClinicalTrials: The Effect of Donepezil on Wound Healing
• Recent EU Clinical Trials: Comparison of therapeutic strategies with Cholinesterase Inhibitors: stop or still (SOS) trial
• Recent NIPH Clinical Trials: A study on donepezil pharmacokinetics and QT time
• Description: Donepezil is another “nonclassic,” centrally acting, reversible, noncompetitive AChEI that was approved in 1997 for treatment of mild-to-moderate AD and dementia. Its selectivity for AChE is 570- to 1,250-fold that for butyrylcholinesterase, and it also exhibits greater affinity for brain AChE than for AChE in the periphery.
• Uses: Donepezil is a cholinesterase inhibitors. Acetylcholine is a neurotransmitter involved in neural signaling throughout the body. Donepezil is a reversible acetylcholinesterase inhibitor that readily crosses the blood-brain barrier to reduce the breakdown of acetylcholine. It has a half-life in circulation of about 70 hours. As acetylcholine modulates plasticity, excitability, and arousal in the central nervous system, donepezil is commonly used in the treatment of Alzheimer’s disease to improve cognition, memory, and behavior. In this way, it is intended to prevent or reverse dementia. Studies on these effects have been equivocal, indicating that more research into the therapeutic potential of donepezil is warranted.[Cayman Chemical]

Technology Process of Donepezil

There total 59 articles about Donepezil 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: 99.0%

ethyl acetate thrice + (±)-2-[(1-benzylpyridin-1-ium-4-yl)methyl]-5,6-dimethoxy-indan-1-one bromide (231283-82-2) → donepezil (120014-06-4,142057-79-2,142057-80-5,142698-19-9)

Guidance literature:

In methanol;

Reference yield: 97.5%

donepezil hydrochloride (142057-77-0) → donepezil (120014-06-4,142057-79-2,142057-80-5,142698-19-9)

Guidance literature:

With sodium hydroxide; In water; ethyl acetate; for 0.5h; pH=11.7; Reagent/catalyst; Solvent; pH-value;

Reference yield: 92.3%

benzyl bromide (100-39-0) + debenzyldonepezil (120014-30-4) → donepezil (120014-06-4,142057-79-2,142057-80-5,142698-19-9)

Guidance literature:

With sodium carbonate; In ethanol; at 50 - 60 ℃; for 6h;

upstream raw materials:

5-[(1-benzyl-4-piperidyl)methyl]-5-(3,4-dimethoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

benzyl bromide

debenzyldonepezil

(E)-2-((1-benzylpiperidine-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Downstream raw materials:

donepezil hydrochloride

1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine hydrochloride monohydrate

1,1-dibenzyl-4-(5,6-dimethoxy-1-oxo-indan-2-ylmethyl)-piperidinium; bromide

Refernces

• 1、 Rao, R. Janaki Rama,Rao, A. K. S. Bhujanga,Murthy. "Efficient and industrially viable synthesis of donepezil". . p. 2847 - 2853. Retrieved 2007.
• 2、 Bailey, J. Daniel,Iyer, Karthik S.,Leahy, David K.,Li, Xiaohan,Lipshutz, Bruce H.,Thakore, Ruchita R.. "Bisulfite Addition Compounds as Substrates for Reductive Aminations in Water". supporting information. p. 7205 - 7208. Retrieved 2021/09/22.
• 3、 -. "METHOD FOR PRODUCING DONEPEZIL BY FLOW REACTION USING IMMOBILIZED CATALYST". Paragraph 0069-0074; 0076-0081; 0083-0089; 0091-0094. . Retrieved 2021/01/08.