Quetiapine → Quetiapine fumarate

HRID 1662945Notes

Reaction equation

HRID 1662945 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[S:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][OH:27])[CH2:18][CH2:17]3)[C:5]=2[CH:6]=1.[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C(O)C.CO>[CH2:18]1[N:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][OH:27])[CH2:20][CH2:21][N:16]([C:7]2[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH2:17]1.[CH2:18]1[N:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][OH:27])[CH2:20][CH2:21][N:16]([C:7]2[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH2:17]1.[CH:29](/[C:28]([OH:35])=[O:34])=[CH:30]\[C:31]([OH:33])=[O:32]

Participants

4

Reactant 2

HCID 5002QuetiapineHCID 444972Fumaric Acid

Product 1

HCID 5281025Quetiapine fumarate

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

In another patent, U.S. Pat. No. 6,372,734, quetiapine hemifumarate is prepared from the crystallized quetiapine base, which is, under boiling, mixed with a solution of fumaric acid in a mixture ethanol/methanol. Crystallized quetiapine hemifumarate is isolated after being cooled to 0° C.

Sources & evidence

ORD record
ord-66664139dd0a47c1bf4e5bd45af07af9
Source dataset
uspto-grants-2011_10
Patent number
US08034805B2

Reaction notes

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