Hydrochloric Acid → Fexofenadine Hydrochloride

HRID 1504919Notes

Reaction equation

HRID 1504919 reaction equation
[OH:1][CH:2]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:37])([CH3:36])[C:33]([OH:35])=[O:34])=[CH:28][CH:27]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.[ClH:38]>C(OCC)(=O)C>[CH3:37][C:32]([C:33]([OH:35])=[O:34])([C:29]1[CH:30]=[CH:31][C:26]([CH:2]([OH:1])[CH2:3][CH2:4][CH2:5][N:6]2[CH2:7][CH2:8][CH:9]([C:12]([OH:25])([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:10][CH2:11]2)=[CH:27][CH:28]=1)[CH3:36].[ClH:38]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3348Fexofenadine

Product 1

HCID 63002Fexofenadine HydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

In a 500 mL four-neck flask equipped with mechanical agitator, a thermometer and a condenser, a suspension of 2-(4-(1-hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid (VI) (9 g, 17.9 mmol) in ethyl acetate (90 mL) was heated to 40° C. Then 30.36% aqueous hydrochloric acid (2 g, 20 mmol) was dropped to the mixture and the final solution was stirred at 40° C. for 1 hour and at room temperature overnight. The crystallized solid was filtered, washed with ethyl acetate and dried under vacuum at 50° C., to give 8.5 g of polymorph φ of Fexofenadine hydrochloride, as a white solid. Yield: 88%.

Workup

  1. customIn a 500 mL four-neck flask equipped with mechanical agitator
  2. filtrationThe crystallized solid was filtered
  3. washwashed with ethyl acetate
  4. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-a27757f9a65347e89b58dc6a66e9198e
Source dataset
uspto-grants-2015_12
Patent number
US09216955B2

Reaction notes

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