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

Base Information

• Chemical Name: 2-((1-Benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
• CAS No.: 145546-80-1
• Molecular Formula: C₂₄H₂₇NO₃
• Molecular Weight: 377.483
• Hs Code.: 2933399090
• European Community (EC) Number: 601-652-4
• UNII: 1D3K90DIY3
• Nikkaji Number: J1.642.719E,J2.840.034I
• Wikidata: Q27252264
• Pharos Ligand ID: 32WXHHQ17AHQ
• ChEMBL ID: CHEMBL168938
• Mol file: 145546-80-1.mol

Synonyms:120014-07-5;2-((1-Benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one;145546-80-1;1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-ylindenemethyl)piperidine;(E)-2-((1-benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one;(2E)-2-[(1-benzylpiperidin-4-yl)methylidene]-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one;1D3K90DIY3;CHEMBL168938;(2E)-2-[(1-benzylpiperidin-4-yl)methylidene]-5,6-dimethoxy-3H-inden-1-one;(E)-2-((1-Benzylpiperidin-4-yl)methylene)-5,6-dimethoxyindan-1-one;1H-Inden-1-one, 2,3-dihydro-5,6-dimethoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methylene]-, (2E)-;(2~{E})-5,6-dimethoxy-2-[[1-(phenylmethyl)piperidin-4-yl]methylidene]-3~{H}-inden-1-one;1H-Inden-1-one, 2,3-dihydro-5,6-dimethoxy-2-((1-(phenylmethyl)-4-piperidinyl)methylene)-, (2E)-;UNII-1D3K90DIY3;2-((1-Benzylpiperidin-4-yl)methylene)-5,6-dimethoxyindan-1-one, (E)-;1-benzyl-4-((5,6-dimethoxy-1-oxoindan-2-ylidene)methyl)piperidine;2-[(1-Benzylpiperidin-4-yl)methylene]-2,3-dihydro-5,6-dimethoxyinden-1-one;BCP28366;VFA54680;BDBM50280646;MFCD08693144;AKOS000277341;CS-W006058;Dehydro Donepezil (Donepezil Impurity);DS-0813;1H-Inden-1-one, 2,3-dihydro-5,6-dimethoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methylene]-;AC-26327;PD134456;CS-0166756;EN300-7363542;Q27252264;DONEPEZIL HYDROCHLORIDE IMPURITY F [EP IMPURITY];2-[(1-Benzyl-4-piperidyl)methylene]-5,6-dimethoxy-1-indanone;(E)-2-(1-Benzyl-4-piperidylmethylene)-5,6-dimethoxy-1-indanone;1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-ylindenemethyl)-piperidine;2-[(1-Benzylpiperidine-4-yl)methylene]-5,6-dimethoxyindan-1-one;DONEPEZIL HYDROCHLORIDE MONOHYDRATE IMPURITY F [EPIMPURITY];1H-Inden-1-one,2,3-dihydro-5,6-dimethoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methylene]-;2-((1-benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydroinden-1-one;2-[1-(1-Benzyl-piperidin-4-yl)-meth-(E)-ylidene]-5,6-dimethoxy-indan-1-one;DZ7

Chemical Property of 2-((1-Benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Chemical Property:

• Boiling Point: 542.8±50.0 °C(Predicted)
• PKA: 8.17±0.10(Predicted)
• PSA: 38.77000
• Density: 1.209±0.06 g/cm3(Predicted)
• LogP: 4.21910
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 377.19909372
• Heavy Atom Count: 28
• Complexity: 560

Purity/Quality:

99.0% Min ^*data from raw suppliers

(2E)-Dehydrodonepezil(DonepezilImpurity) ^*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(=CC3CCN(CC3)CC4=CC=CC=C4)C2=O)OC
• Isomeric SMILES: COC1=C(C=C2C(=C1)C/C(=C\C3CCN(CC3)CC4=CC=CC=C4)/C2=O)OC
• Uses: (2E)-Dehydrodonepezil (Donepezil USP Related Compound A) is a derivative of Donepezil (D531750), a nootropic. An inhibitor of acetylcholinesterase.

Technology Process of 2-((1-Benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

There total 19 articles about 2-((1-Benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one 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: 100.0%

5,6-dimethoxy-1-indanone (2107-69-9) + N-benzyl-4-formylpiperidine (22065-85-6) → 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine (120014-07-5,145546-80-1)

Guidance literature:

With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In water; toluene; at 20 ℃; Product distribution / selectivity; Inert atmosphere; Reflux;

Reference yield: 92.5%

5,6-dimethoxy-1-indanone (2107-69-9) + N-benzyl-4-formylpiperidine (22065-85-6) → (E)-2-((1-benzylpiperidine-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (145546-80-1)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 0 - 25 ℃; for 1.25h; Product distribution / selectivity;

Reference yield: 89.0%

N-benzyl-4-formylpiperidine (22065-85-6) + 3-chloro-1-(3,4-dimethoxyphenyl)propan-1-one (4693-38-3) → 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine (120014-07-5,145546-80-1)

Guidance literature:

With triethylammonium tetrachloroaluminate; at 55 - 175 ℃; for 11h; Temperature; Reagent/catalyst; Concentration; Inert atmosphere;

upstream raw materials:

5,6-dimethoxy-1-indanone

N-benzyl-4-formylpiperidine

4-carbethoxypiperidine

benzyl chloride

Refernces

• 1、 -. "Purification method of donepezil hydrochloride key intermediate compound (by machine translation)". Paragraph 0031-0037. . Retrieved 2020/08/17.
• 2、 Gaonkar, Santosh L.,Nadaf,Bilehal, Dinesh,Shetty, Nitinkumar S.. "Industrially scalable synthesis of anti-alzheimer drug donepezil". . p. 1999 - 2004. Retrieved 2017/07/27.