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CAS 2107-69-9

5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Codes: DONE-006

Application context (from source-drug indications)

Alzheimer's diseaseMemantine Hydrochloride/Donepezil HydrochlorideLewy body dementiaDonepezil HydrochlorideAlzheimer's diseaseDonepezil HydrochlorideDementiaDonepezil HydrochlorideMemory impairmentDonepezil HydrochlorideMild cognitive impairmentDonepezil HydrochlorideOsteoporosisDonepezil Hydrochloride

Source drugs (routes using this intermediate)

DrugTierExpiry
Memantine Hydrochloride/Donepezil HydrochlorideTier C — Watch / trade-
Donepezil HydrochlorideTier B — Position early-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

Memantine Hydrochloride/Donepezil HydrochlorideOriginator routesteps: 5total yield: 0.36 g
ethyl piperidine-4-carboxylate→(chloromethyl)benzene→ethyl 1-benzylpiperidine-4-carboxylate→(1-benzylpiperidin-4-yl)methanol→1-benzylpiperidine-4-carbaldehyde→5,6-dimethoxy-2,3-dihydro-1H-inden-1-one→(E)-2-((1-benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
Memantine Hydrochloride/Donepezil HydrochlorideOptimised routesteps: 4total yield: 10.00 g
5,6-dimethoxy-2,3-dihydro-1H-inden-1-one→isonicotinaldehyde→(E)-5,6-dimethoxy-2-(pyridin-4-ylmethylene)-2,3-dihydro-1H-inden-1-one→5,6-dimethoxy-2-(pyridin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one→5,6-dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one→(bromomethyl)benzene
Memantine Hydrochloride/Donepezil HydrochlorideOptimised routesteps: 5total yield: 0.90 g
1-benzylpiperidine-4-carbaldehyde→5,6-dimethoxy-2,3-dihydro-1H-inden-1-one→(E)-2-((1-benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one→1-benzylpiperidin-4-one→ethyl 2-chloroacetate→ethyl 6-benzyl-1-oxa-6-azaspiro[2.5]octane-2-carboxylate→sodium 6-benzyl-1-oxa-6-azaspiro[2.5]octane-2-carboxylate
Memantine Hydrochloride/Donepezil HydrochlorideOptimised routesteps: 4total yield: 80.00 g
5,6-dimethoxy-2,3-dihydro-1H-inden-1-one→isonicotinaldehyde→(bromomethyl)benzene→1-benzyl-4-formylpyridin-1-ium bromide→(E)-1-benzyl-4-((5,6-dimethoxy-1-oxo-1H-inden-2(3H)-ylidene)methyl)pyridin-1-ium bromide→(E)-2-((1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
Donepezil HydrochlorideOriginator routesteps: 5total yield: 0.36 g
ethyl piperidine-4-carboxylate→(chloromethyl)benzene→ethyl 1-benzylpiperidine-4-carboxylate→(1-benzylpiperidin-4-yl)methanol→1-benzylpiperidine-4-carbaldehyde→5,6-dimethoxy-2,3-dihydro-1H-inden-1-one→(E)-2-((1-benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
Donepezil HydrochlorideOptimised routesteps: 4total yield: 10.00 g
5,6-dimethoxy-2,3-dihydro-1H-inden-1-one→isonicotinaldehyde→(E)-5,6-dimethoxy-2-(pyridin-4-ylmethylene)-2,3-dihydro-1H-inden-1-one→5,6-dimethoxy-2-(pyridin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one→5,6-dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one→(bromomethyl)benzene
Donepezil HydrochlorideOptimised routesteps: 5total yield: 0.90 g
1-benzylpiperidine-4-carbaldehyde→5,6-dimethoxy-2,3-dihydro-1H-inden-1-one→(E)-2-((1-benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one→1-benzylpiperidin-4-one→ethyl 2-chloroacetate→ethyl 6-benzyl-1-oxa-6-azaspiro[2.5]octane-2-carboxylate→sodium 6-benzyl-1-oxa-6-azaspiro[2.5]octane-2-carboxylate
Donepezil HydrochlorideOptimised routesteps: 4total yield: 80.00 g
5,6-dimethoxy-2,3-dihydro-1H-inden-1-one→isonicotinaldehyde→(bromomethyl)benzene→1-benzyl-4-formylpyridin-1-ium bromide→(E)-1-benzyl-4-((5,6-dimethoxy-1-oxo-1H-inden-2(3H)-ylidene)methyl)pyridin-1-ium bromide→(E)-2-((1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

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