1,4-Dioxane hydrochloride → HCID 66906008, compound

HRID 1691686Notes

Reaction equation

HRID 1691686 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=2)[CH2:26][CH2:25][N:24]([C:35]([O:37][C:38]2[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=2)=[O:36])[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:47].O1CCOCC1>>[ClH:47].[F:34][C:30]1[CH:29]=[C:28]([CH:27]2[CH2:26][CH2:25][N:24]([C:35]([O:37][C:38]3[CH:39]=[CH:40][C:41]([C:42]([OH:44])=[O:43])=[CH:45][CH:46]=3)=[O:36])[CH2:23][CH:22]2[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])[CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66906261HCID 66906261, compound

Product 1

HCID 66906008HCID 66906008, compound

Procedure

To 385 mg of 4-({[3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-(3-fluorophenyl)piperidin-1-yl]carbonyl}oxy)benzoic acid was added 2.0 mL of a 4 M hydrogen chloride/1,4-dioxane solution, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added isopropanol, followed by heating for dissolution. Diisopropylether was added dropwise thereto, and the precipitate was isolated by filtration, and dried under reduced pressure to obtain 178 mg of 4-({[4-(3-fluorophenyl)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]carbonyl}oxy)benzoic acid hydrochloride as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added isopropanol
  3. temperatureby heating for dissolution
  4. additionDiisopropylether was added dropwise
  5. customthe precipitate was isolated by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-4fb025cd0a9e45d1b6ab8d3a877eeac6
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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