Hydrochloric Acid → Fexofenadinone Hydrochloride

HRID 2306069Notes

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

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 (2.5L) 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 (1L) 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

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

Sources & evidence

ORD record: ord-1e95a290eb084166bb2b2e6acde4dab0
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441179B1

Reaction notes

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