Hydrochloric Acid → Fexofenadinone Hydrochloride

HRID 1857871Notes

Reaction equation

HRID 1857871 reaction equation
C[O:2][C:3](=[O:38])[C:4]([CH3:37])([CH3:36])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:35])[CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([C:21]([OH:34])([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)=[CH:7][CH:6]=1.[OH-].[Na+].[ClH:41]>CO>[ClH:41].[OH:34][C:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][CH2:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([CH3:37])([CH3:36])[C:3]([OH:38])=[O:2])=[CH:6][CH:7]=2)=[O:35])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 99581012-[4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]-2,2-dimethylacetic acid methyl ester

Product 1

HCID 10230449Fexofenadinone Hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
68 °C

Procedure

Dissolve 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid methyl ester (0.131 mol) in methanol (2.5 L) and add 10% sodium hydroxide (769 mL, 1.92 mol). Stir at reflux for 1.5 hours, cool to 68° C. and evaporate the solvent in vacuo to a residue. Add chloroform (1 L) and stir until the solids are dissolved. Separate the organic phase and extract the aqueous phase with chloroform (3×300 mL). Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo to give a residue. Treat the residue with ethereal HCl, filter and dry to give the title compound.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customevaporate the solvent in vacuo to a residue
  3. stirringAdd chloroform (1 L) and stir until the solids
  4. dissolutionare dissolved
  5. customSeparate the organic phase
  6. extractionextract the aqueous phase with chloroform (3×300 mL)
  7. dry with materialCombine the organic phases, dry (MgSO4)
  8. customevaporate the solvent in vacuo
  9. customto give a residue
  10. filtrationfilter
  11. customdry

Sources & evidence

ORD record
ord-b9cb09773dac40209f3aaa42b5e7be04
Source dataset
uspto-grants-2000_11
Patent number
US06147216

Reaction notes

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