Ethanol → HCID 69566592, compound

HRID 271036Notes

Reaction equation

HRID 271036 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1.[ClH:23].[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28].C(O)C>>[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:15][CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1.[ClH:23].[C:24]([OH:31])(=[O:30])[CH2:25][CH2:26][C:27]([OH:29])=[O:28].[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:15][CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1.[ClH:23].[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28]

Participants

6

Reactant 3

HCID 702EthanolHCID 62857Fluoxetine hydrochlorideHCID 444972Fumaric Acid

Product 3

HCID 1110Succinic AcidHCID 62857Fluoxetine hydrochlorideHCID 69566592HCID 69566592, compoundYield 82%

Procedure

Cocrystals of fluoxetine HCl and succinic acid were prepared as follows. A 6.00 g sample of fluoxetine HCl and 1.01 g of fumaric acid were dissolved in 20 mL of ethanol with heating. The solution was filtered through a 0.2 μm nylon filter, concentrated to a volume of 8 mL, and cooled in an ice bath for 6 hours. The solid material was isolated on filter paper and allowed to dry in the air to give 5.74 g (82% yield) of fluoxetine HCl:fumaric acid (2:1) cocrystal. The measured melting points were 158° C. for fluoxetine HCl, >300° C. (decomposes) for fumaric acid, and 164° C. for the cocrystal. The cocrystal is expected to have a good toxicology profile, since fumaric acid is known to be safe and appears on the Generally Recognized As Safe (“GRAS”) list from the U.S. Food and Drug Administration.

Workup

  1. temperaturewith heating
  2. filtrationThe solution was filtered through a 0.2 μm nylon
  3. filtrationfilter
  4. concentrationconcentrated to a volume of 8 mL
  5. temperaturecooled in an ice bath for 6 hours
  6. customThe solid material was isolated
  7. filtrationon filter paper
  8. customto dry in the air

Sources & evidence

ORD record
ord-c01a9baffe2f4da691b8cb4f52580ce0
Source dataset
uspto-grants-2008_11
Patent number
US07452555B2

Reaction notes

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