1,4-Dioxane hydrochloride → HCID 66906388, compound

HRID 1691719Notes

Reaction equation

HRID 1691719 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([NH: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>>[ClH:46].[C:11]1([C@H:9]([NH:8][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([NH: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

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66906180HCID 66906180, compound

Product 1

HCID 66906388HCID 66906388, compound

Procedure

To 289 mg of the crude product of 4-({[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]carbonyl}amino)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 the residue was then heated under reflux for dissolution in isopropanol. Diisopropylether was added dropwise thereto, and the precipitate was isolated by filtration, and dried under reduced pressure to obtain 159 mg of 4-({[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]carbonyl}amino)benzoic acid hydrochloride as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. temperaturethe residue was then heated
  3. temperatureunder reflux for dissolution in isopropanol
  4. additionDiisopropylether was added dropwise
  5. customthe precipitate was isolated by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-a091a65e21914eaaa5f2fd715d0ef64f
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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