Sulfuric Acid → Methyl 4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidine-1-carboxylate

HRID 269381Notes

Reaction equation

HRID 269381 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[C:6]([C:8](=[CH2:20])[CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1)=[O:7].S(=O)(=O)(O)O>>[CH3:25][O:24][C:23]1[CH:22]=[C:21]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C:6](=[O:7])[CH:8]([CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1)[CH2:20]2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 10914993HCID 10914993, compound

Product 1

HCID 11078542Methyl 4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidine-1-carboxylate

Procedure

According to WO 9722584, methyl 4-[2-(3,4-dimethoxybenzoyl)ally]piperidin-1-carboxylate is cyclized in the presence of sulfuric acid to give methyl 4-(5,6-dimethoxy-1-oxoindan-2-ylmethyl)piperidin-1-carboxylate, decarboxylated and then treated with benzyl bromide to give donepezil.

Sources & evidence

ORD record
ord-af21d47602d645899f905ed1de520f51
Source dataset
uspto-grants-2008_11
Patent number
US07446203B2

Reaction notes

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