Fexofenadine → Fexofenadine Hydrochloride

HRID 644792Notes

Reaction equation

HRID 644792 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].C(O)(C)C>C1(C)C=CC=CC=1>[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 1140TolueneSolvent

Procedure

To pure Fexofenadine (50 g), toluene (500 ml) is added and the mixture is refluxed azeotropically for about 3 hours. The reaction mass is then cooled to room temperature followed by slow addition of isopropanol hydrogen chloride, to pH 2. The reaction mass is then stirred for about 15 and a half hours. The separated solid is filtered, washed with toluene (50 ml) and dried (Yield 43.3 g). Part of this solid (42 g) is suspended in ethyl acetate (420 ml) and refluxed for about 1 hour (this operation was performed for removal of residual organic solvents). The suspension is then cooled to room temperature and stirred for 20 minutes. The reaction mass is filtered and washed with ethyl acetate (42 ml). The desired Form X of Fexofenadine hydrochloride is dried at 90-96° C. to constant weight.

Workup

  1. temperaturethe mixture is refluxed azeotropically for about 3 hours
  2. filtrationThe separated solid is filtered
  3. washwashed with toluene (50 ml)
  4. customdried (Yield 43.3 g)
  5. temperaturerefluxed for about 1 hour (this operation
  6. customwas performed for removal of residual organic solvents)
  7. temperatureThe suspension is then cooled to room temperature
  8. stirringstirred for 20 minutes
  9. filtrationThe reaction mass is filtered
  10. washwashed with ethyl acetate (42 ml)
  11. dry with materialThe desired Form X of Fexofenadine hydrochloride is dried at 90-96° C. to constant weight

Sources & evidence

ORD record
ord-b7d87e97d7804cac9719ffab02fbd187
Source dataset
uspto-grants-2010_04
Patent number
US07700779B2

Reaction notes

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