5,6-Dimethoxy-1-indanone → 2-((1-Benzylpiperidin-4-yl)methylene)-5,6-dimethoxyindan-1-one, (E)-

HRID 269379Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH2:7][CH2:6]2.[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([N-]C(C)C)(C)C.[Li+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[C:7](=[CH:28][CH:25]1[CH2:24][CH2:23][N:22]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:27][CH2:26]1)[CH2:6]2

Participants

Reactant 3

HCID 750185,6-Dimethoxy-1-indanone

HCID 895841-Benzylpiperidine-4-carbaldehyde

HCID 2724682Lithium diisopropylamide

Product 1

HCID 533948492-((1-Benzylpiperidin-4-yl)methylene)-5,6-dimethoxyindan-1-one, (E)-

Procedure

According to the process disclosed in U.S. Pat. No. 4,895,841, 5,6-dimethoxy-1-indanone was condensed with 1-benzyl-4-formylpiperidine in the presence of lithium diisopropylamide to give 5,6-dimethoxy-2-[[1-benzyl-4-piperidinyl]methylene]-1-indanone, which was then reduced with platinum oxide catalyst to give donepezil.

Sources & evidence

ORD record: ord-8c3ead6fe54e4b57841ba89c8765abfe
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446203B2

Reaction notes

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