Donepezil → 5,6-Dimethoxy-2-(4-pyridyl)methylene-1-indanone

HRID 269380Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH2:14][CH:13]([CH2:15][CH:16]3[CH2:21][CH2:20][N:19](CC4C=CC=CC=4)[CH2:18][CH2:17]3)[C:11](=[O:12])[C:6]2=[CH:7][C:8]=1[O:9][CH3:10].COC1C=C2C(=CC=1OC)C(=O)CC2.N1C=CC(C=O)=CC=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[O:9][CH3:10])[C:11](=[O:12])[C:13](=[CH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH2:14]2

Participants

Reactant 3

HCID 3152Donepezil

HCID 133894-Pyridinecarboxaldehyde

HCID 750185,6-Dimethoxy-1-indanone

Product 1

HCID 533951325,6-Dimethoxy-2-(4-pyridyl)methylene-1-indanone

Procedure

U.S. Pat. No. 5,606,064 disclosed a process for the preparation of donepezil. 5,6-dimethoxy-1-indanone was condensed with pyridin-4-aldehyde to give 5,6-dimethoxy-2-(pyridin-4-yl)methyleneindan-1-one, reacted with benzyl bromide to give 1-benzyl-4-(5,6-dimethoxyindan-1-on-2-ylidene)methylpyridinium bromide and then, hydrogenated in the presence of platinum oxide catalyst to yield donepezil.

Sources & evidence

ORD record: ord-55926d35552f411986f67c3cab95f973
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446203B2

Reaction notes

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