1,4-Dioxane hydrochloride → 3,5-difluoro-4-[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]benzoic acid hydrochloride

HRID 1691692Notes

Reaction equation

HRID 1691692 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

HCID 204431481,4-Dioxane hydrochlorideHCID 669059254-[3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]-3,5-difluorobenzoic acid

Product 1

HCID 669064423,5-difluoro-4-[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]benzoic acid hydrochloride

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.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, to the residue
  2. additionwere added THF, isopropanol, and diisopropylether
  3. customthe precipitated solid was isolated by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-28ad5f8b6bf94c49bc79578572a1d822
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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