Hydrochloric Acid → Fexofenadine Hydrochloride

HRID 2356368Notes

Reaction equation

HRID 2356368 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(#N)C.C(OC(C)C)(C)C>[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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 3348Fexofenadine

Product 1

HCID 63002Fexofenadine Hydrochloride

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 7914Diisopropyl EtherSolvent

Procedure

86 g of fexofenadine base were suspended in acetonitrile (700 g), and 30 g of a 20.6 percent solution of hydrogen chloride in diisopropyl ether were added at −10 to −12° C. The reaction mixture was heated at the reflux temperature for 1 h and then cooled. The hydrochloride was isolated by filtration, washed with acetonitrile and dried under vacuum at 100° C. to give 83 g (90%) of fexofenadine hydrochloride, form A.

Workup

  1. temperatureThe reaction mixture was heated at the reflux temperature for 1 h
  2. temperaturecooled

Sources & evidence

ORD record
ord-3733766c9f1044d8943eb6281d4d7616
Source dataset
uspto-grants-2010_07
Patent number
US07759364B2

Reaction notes

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