Sodium Hydroxide → Fexofenadine

HRID 126830Notes

Reaction equation

HRID 126830 reaction equation
[OH:1][C:2]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:27])([CH3:26])[C:21]([O:23]CC)=[O:22])=[CH:16][CH:15]=2)[OH:13])[CH2:5][CH2:4]1.[OH-].[Na+]>C(O)C>[OH:1][C:2]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:27])([CH3:26])[C:21]([OH:23])=[O:22])=[CH:16][CH:15]=2)[OH:13])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9849889Ethyl Fexofenadine

Product 1

HCID 3348Fexofenadine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.6 g of ethyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetate in 20 ml of absolute ethanol is added 10 ml of a 50% solution of sodium hydroxide. The mixture is refluxed for 31/2 hours and concentrated to a solid after which a minimum amount of methanol to dissolve the residue is added. 10% Aqueous HCl is added until pH 7 is reached, the methanol removed by evaporation and water (25 ml) is added. The resulting precipitate is recrystallized from methanol-butanone to give 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetic acid, M.P. 195°-197° C.

Workup

  1. temperatureThe mixture is refluxed for 31/2 hours
  2. concentrationconcentrated to a solid after which a minimum amount of methanol
  3. dissolutionto dissolve the residue
  4. additionis added
  5. addition10% Aqueous HCl is added until pH 7
  6. customthe methanol removed by evaporation and water (25 ml)
  7. additionis added
  8. customThe resulting precipitate is recrystallized from methanol-butanone

Sources & evidence

ORD record
ord-a03daa640a6549e7a897dd2fdf501166
Source dataset
uspto-grants-1981_03
Patent number
US04254129

Reaction notes

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