Fexofenadine → Fexofenadine Hydrochloride

HRID 2242092Notes

Reaction equation

HRID 2242092 reaction equation
[CH3:1][C:2]([C:35]([OH:37])=[O:36])([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([OH:34])[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20]([OH:33])([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:16][CH2:15]2)=[CH:8][CH:9]=1)[CH3:3].[ClH:38].CC(O)C>CO>[CH3:3][C:2]([C:35]([OH:37])=[O:36])([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:34])[CH2:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:20]([OH:33])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:18][CH2:19]2)=[CH:6][CH:5]=1)[CH3:1].[ClH:38]

Participants

4

Reactant 2

HCID 3348FexofenadineHCID 21912024Isopropanol hydrochloride

Product 1

HCID 63002Fexofenadine Hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Fexofenadine free base (20 grams) was crushed and put into a 250 ml round bottom flask in an ice bath with a magnetic stirrer. HCl/IPA (6.5 ml) was added to 80 ml methanol and cooled in an ice bath, and then added to the flask with mixing. After 15 minutes, the flask was filtered, and the filtrate evaporated off at room temperature first with a water aspirator then with a diaphragm pump and finally with an oil pump. The remaining material (5 grams) was stirred as a slurry overnight with a mixture of heptane (15 ml) and methanol (1.5 ml), filtered and dried for 1 hour at 65° C. under vacuum. PXRD analysis confirmed presence of Form XVI of fexofenadine hydrochloride.

Workup

  1. customput into a 250 ml round bottom flask in an ice bath with a magnetic stirrer
  2. temperaturecooled in an ice bath
  3. additionadded to the flask
  4. additionwith mixing
  5. filtrationthe flask was filtered
  6. customthe filtrate evaporated off at room temperature first with a water aspirator then with a diaphragm pump
  7. filtrationfiltered
  8. customdried for 1 hour at 65° C. under vacuum

Sources & evidence

ORD record
ord-f6207e6ea41c450caa99d15f16b64839
Source dataset
uspto-grants-2010_03
Patent number
US07671071B2

Reaction notes

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