1,4-Dioxane hydrochloride → 3,5-difluoro-4-[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]benzoic acid hydrochloride
Reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][CH2:25][N:24]([C:34]2[C:42]([F:43])=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[CH:36][C:35]=2[F:44])[CH2:23]1)[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.[ClH:45].O1CCOCC1>>[ClH:45].[F:43][C:42]1[CH:41]=[C:37]([CH:36]=[C:35]([F:44])[C:34]=1[N:24]1[CH2:25][CH2:26][CH:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:22]([CH2:21][NH:8][C@@H:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH2:23]1)[C:38]([OH:40])=[O:39]Participants
3
Reactant 2
Product 1
Procedure
To 127 mg of 4-[3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]-3,5-difluorobenzoic acid was added 3.0 mL of a 4 M hydrogen chloride/1,4-dioxane solution, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, to the residue were added THF, isopropanol, and diisopropylether, and the precipitated solid was isolated by filtration, and dried under reduced pressure to obtain 78 mg of 3,5-difluoro-4-[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]benzoic acid hydrochloride as a pale pink solid.