Ethanol → HCID 21570871, compound

HRID 1803478Notes

Reaction equation

HRID 1803478 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].[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 21570871HCID 21570871, 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 0.8 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 flucxetine 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 0.8 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-83f2f724b2c6484eaac4219943f78fd4
Source dataset
uspto-grants-2013_01
Patent number
US08350085B2

Reaction notes

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