Sodium Hydroxide → Fexofenadine

HRID 1840930Notes

Reaction equation

HRID 1840930 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]([CH:9](O)[CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:26])([CH3:25])[C:20]([O:22]CC)=[O:21])=[CH:15][CH:14]=2)[CH2:5][CH2:4]1.[OH-:40].[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:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:3]1[CH2:4][CH2:5][N:6]([CH2:9][CH2:10][CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:25])([CH3:26])[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=2)[OH:40])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10165357Ethyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-hydroxybutyl]-alpha,alpha-dimethylbenzeneacetate

Product 1

HCID 3348Fexofenadine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to the described procedure of Carr et al., U.S. Pat. No. 4,254,129, to a solution of 0.6 g of ethyl 4-[4[4-(hydroxydiphenylmethyl)-1-piperidinyl]-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 3½ 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 methanolbutanone 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 3½ 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 methanolbutanone

Sources & evidence

ORD record
ord-a7d4e1f534f0402eac1183b62ff11f26
Source dataset
uspto-grants-2004_01
Patent number
US06683094B2

Reaction notes

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