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

HRID 1760732Notes

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

Patent application EP 711756 describes the preparation of Donepezil by reaction of 5,6-dimethoxy-1-indanone with pyridin-4-aldehyde to give 5,6-dimethoxy-2-(pyridin-4-yl)methylene indan-1-one. Reaction with benzyl bromide afforded 1-benzyl-4-(5,6-dimethoxyindan-1-on-2-ylidene)methylpyridinium bromide. Hydrogenation in the presence of platinum oxide afforded Donepezil (Scheme 4).

Sources & evidence

ORD record: ord-50cda0d5b8fd4ea7afe97eb1768d1805
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06844440B2

Reaction notes

Loading…