Toluene → Fexofenadine Hydrochloride

HRID 644791Notes

Reaction equation

HRID 644791 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].C1(C)C=CC=CC=1.[ClH:45].C(O)(C)C>C(OCC)(=O)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:45]

Participants

5

Reactant 3

HCID 1140TolueneHCID 3348FexofenadineHCID 21912024Isopropanol hydrochloride

Product 1

HCID 63002Fexofenadine Hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the Fexofenadine Form A (170 g; prepared as per procedure in step 1), toluene (1700 ml) is added followed by slow addition of isopropanol hydrogen chloride (prepared by purging hydrogen chloride to isopropyl alcohol) to pH 2. The reaction mass is then stirred for 10 hours 15 minutes. The solid obtained is filtered, washed with toluene (170 ml) and dried under vacuum at 75-80° C. Solid thus obtained (140 g) is refluxed in ethyl acetate (2800 ml) for about 1 hour. The reaction mixture is then cooled to room temperature and stirred for 1 hour 30 minutes. The reaction mass is filtered and washed with ethyl acetate (140 ml). The desired Form X of Fexofenadine hydrochloride is obtained after drying at 78-85° C. under atmospheric pressure till constant weight.

Workup

  1. additionis added
  2. customThe solid obtained
  3. filtrationis filtered
  4. washwashed with toluene (170 ml)
  5. customdried under vacuum at 75-80° C
  6. customSolid thus obtained (140 g)
  7. stirringstirred for 1 hour 30 minutes
  8. filtrationThe reaction mass is filtered
  9. washwashed with ethyl acetate (140 ml)

Sources & evidence

ORD record
ord-a82b5e2480af46be9839e8f88c1ad9d5
Source dataset
uspto-grants-2010_04
Patent number
US07700779B2

Reaction notes

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