4-[(4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylbenzeneacetic acid hydrochloride hydrate → Fexofenadine Hydrochloride

HRID 1444092Notes

Reaction equation

O.[ClH:2].[OH:3][C:4]([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:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:27])([CH3:26])[C:23]([OH:25])=[O:24])=[CH:18][CH:17]=2)[OH:15])[CH2:7][CH2:6]1>CC(CC)=O>[ClH:2].[OH:3][C:4]([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:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:27])([CH3:26])[C:23]([OH:25])=[O:24])=[CH:18][CH:17]=2)[OH:15])[CH2:7][CH2:6]1

Participants

Conditions

Temperature: -15 °C

Procedure

Treat 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetic acid hydrochloride hydrate (Form II) (5.00 g, 0.0083 mol) with methylethyl ketone (130 mL). Slowly add water (0.4 mL), filter through filter aid and wash the filter cake with methylethyl ketone (20 mL). Heat to reflux and distill off 75 mL of solvent, cool to −15° C. and collect by vacuum filtration. Wash with methylethyl ketone (2×10 mL) and vacuum dry at 60° C. to give the title compound (4.33 g, 97%); mp 196-198° C.

Workup

filtrationSlowly add water (0.4 mL), filter
filtrationthrough filter aid
washwash the filter cake with methylethyl ketone (20 mL)
temperatureHeat
temperatureto reflux
distillationdistill off 75 mL of solvent
filtrationcollect by vacuum filtration
washWash with methylethyl ketone (2×10 mL) and vacuum
customdry at 60° C.

Sources & evidence

ORD record: ord-6c4dff596c704da6805633eee9a2ca38
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662835B2

Reaction notes

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