Sodium Hydroxide → Fexofenadine

HRID 1836787Notes

Reaction equation

HRID 1836787 reaction equation
[BH4-].[Na+].[OH-].[Na+].Cl.[OH:6][C:7]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH3:30])([CH3:29])[C:26]([OH:28])=[O:27])=[CH:21][CH:20]=2)=[O:18])[CH2:10][CH2:9]1>O.C(O)C>[OH:6][C:7]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH3:30])([CH3:29])[C:26]([OH:28])=[O:27])=[CH:21][CH:20]=2)[OH:18])[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 10230449Fexofenadinone Hydrochloride

Product 1

HCID 3348Fexofenadine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Add sodium borohydride (0.105 g, 2.77 mmol) to a solution of sodium hydroxide (0.053 g, 1.33 mmol) in deionized water (2 mL) and add, by dropwise addition, to a solution of 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid hydrochloride (0.70 g, 1.31 mmol) in ethanol (30 mL). Stir at room temperature for 3.5 hours at pH 7-8. Evaporate the solvent in vacuo and stir the residue with methylene chloride (15 mL) and deionized water (15 mL). Dry (MgSO4), acidify to pH 3 with gaseous hydrogen chloride and evaporate the solvent. Add ether with stirring, filter the white solid and wash with additional ether. Dry to give the title compound.

Workup

  1. customEvaporate the solvent in vacuo
  2. stirringstir the residue with methylene chloride (15 mL) and deionized water (15 mL)
  3. dry with materialDry (MgSO4)
  4. customevaporate the solvent
  5. stirringAdd ether with stirring
  6. filtrationfilter the white solid
  7. washwash with additional ether
  8. customDry

Sources & evidence

ORD record
ord-e587a19619bb440ca7245c14e77f1145
Source dataset
uspto-grants-2004_08
Patent number
US06777555B2

Reaction notes

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