120012-04-6

Basic information

• Product Name: Dihydro Donepezil (Mixture of Diastereomers)
• Synonyms: 2,3-Dihydro-5,6-diMethoxy-2-[[1-(phenylMethyl)-4-piperidinyl]Methyl]-1H-inden-1-ol;Donepezil Dihydro IMpurity;Donepezil IMpurity-VI;1H-Inden-1-ol, 2,3-dihydro-5,6- diMethoxy-2-[[1-(phenylMethyl)-4-piperidinyl]Methyl]-;Dihydro Donepezil;Dihydro Donepezil (Mixture of Diastereomers);2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-ol
• CAS NO: 120012-04-6
• Molecular Formula: C₂₄H₃₁NO₃
• Molecular Weight: 381.50784
• Product Categories: Pharmaceuticals;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities
• Mol File: 120012-04-6.mol

Chemical Properties

• Boiling Point: 520.367°C at 760 mmHg
• Flash Point: 268.509°C
• Appearance: /
• Density: 1.146g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol (Slightly, Heated)
• PKA: 14.03±0.40(Predicted)
• CAS DataBase Reference: Dihydro Donepezil (Mixture of Diastereomers)(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydro Donepezil (Mixture of Diastereomers)(120012-04-6)
• EPA Substance Registry System: Dihydro Donepezil (Mixture of Diastereomers)(120012-04-6)

Safety Data

• Hazardous Substances Data: 120012-04-6(Hazardous Substances Data)

Usage

Uses

A potential metabolite of Donepezil.

InChI:InChI=1/C24H31NO3/c1-27-22-14-19-13-20(24(26)21(19)15-23(22)28-2)12-17-8-10-25(11-9-17)16-18-6-4-3-5-7-18/h3-7,14-15,17,20,24,26H,8-13,16H2,1-2H3

Upstream product

• 120014-07-5 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine 
• 22065-85-6 N-benzyl-4-formylpiperidine 
• 2107-69-9 5,6-dimethoxy-1-indanone 
• 120014-06-4 donepezil 

Downstream Products

• 142057-77-0 donepezil hydrochloride 
• 120014-06-4 donepezil 
• 130927-68-3 1-Benzyl-4-[(5,6-dimethoxyinden)-2-yl]methylpiperidine hydrochloride 

Relevant articles and documents

Synthetic method of donepezil hydrochloride

The invention belongs to the technical field of medicines, and discloses a synthetic method of donepezil hydrochloride. The method comprises the following steps: taking 5, 6-dimethoxy-1-indanone and 4-pyridylaldehyde as initial raw materials, generating a

CRYSTALLINE FORM OF DONEPEZIL HYDROCHLORIDE

A process for preparing crystalline form I of donepezil hydrochloride comprises: a) condensing 5,6-dimethoxy-2-piperidin-4-yl-methyl-indan-1-one with benzyl bromide and reacting a condensation product with hydrobromic acid to form donepezil hydrobromide; and b) hydrolyzing donepezil hydrobromide, followed by reacting with aqueous hydrochloric acid.

Synthesis and structure-activity relationships of acetylcholinesterase inhibitors: 1-Benzyl-4-[(5,6-dimethoxy-1-oxoindan-2-yl)methyl]piperidine hydrochloride and related compounds

Following the discovery of a new series of anti-acetylcholinesterase (anti-AChE) inhibitors such as 1-benzyl-4-[2-(N-benzoylamino)ethyl]piperidine (1), we reported that its rigid analogue, 1-benzyl-4-(2-isoindolin-2- ylethyl)piperidine (5), had more potent activity. We have extended the structure-activity relationship (SAR) study for the rigid analogue and found that the 2-isoindoline moiety in compound 5 can be replaced with a indanone moiety (8) without a major loss in potency. Among the indanone derivatives, 1-benzyl-4-[(5,6-dimethoxy-1-oxoindan-2-yl)methyl]piperidine (13e) (E2020) (IC50 = 5.7 nM) was found to be one of the most potent anti-AChE inhibitors. Compound 13e showed a selective affinity 1250 times greater for AChE than for butyrylcholinesterase. In vivo studies demonstrated that 13e has a longer duration of action than physostigmine at a dose of 5 mg/kg (po) and produced a marked and significant increase in acetylcholine content in rat cerebral cortex. We report the synthesis, SAR, and a proposed hypothetical binding site of 13e (E2020).