1,4-Dioxane hydrochloride → HCID 66905999, compound

HRID 1691713Notes

Reaction equation

HRID 1691713 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]2[CH:39]=[CH:38][C:34]([C:35]([OH:37])=[O:36])=[CH:33][CH:32]=2)=[O:29])[CH2:24][CH:23]1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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:46].O1CCOCC1>O1CCOCC1>[ClH:46].[C:11]1([C@H:9]([NH:8][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]3[CH:32]=[CH:33][C:34]([C:35]([OH:37])=[O:36])=[CH:38][CH:39]=3)=[O:29])[CH2:24][CH:23]2[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH3:10])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66906215HCID 66906215, compound

Product 1

HCID 66905999HCID 66905999, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 193 mg of 4-({[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]carbonyl}oxy)benzoic acid was added 2.0 mL of a 1,4-dioxane, and 2.0 mL of a 4 M hydrogen chloride/1,4-dioxane solution, followed by stirring at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, the residue was heated in isopropanol under reflux, and the mixture was left to be cooled at room temperature. The precipitate was collected by filtration, and dried under reduced pressure to obtain 117 mg of 4-({[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]carbonyl}oxy)benzoic acid hydrochloride as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. temperaturethe residue was heated in isopropanol
  3. temperatureunder reflux
  4. waitthe mixture was left
  5. temperatureto be cooled at room temperature
  6. filtrationThe precipitate was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-dddbdfa0fa2644f38f48b94759254a50
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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