1,4-Dioxane hydrochloride → HCID 66906152, compound

HRID 1691684Notes

Reaction equation

HRID 1691684 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]([O:36][C:37]2[CH:45]=[CH:44][C:40]([C:41]([OH:43])=[O:42])=[CH:39][CH:38]=2)=[O:35])[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:46].O1CCOCC1>>[ClH:46].[C:11]1([C@H:9]([NH:8][CH2:21][CH:22]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:26][CH2:25][N:24]([C:34]([O:36][C:37]3[CH:38]=[CH:39][C:40]([C:41]([OH:43])=[O:42])=[CH:44][CH:45]=3)=[O:35])[CH2:23]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 66906299HCID 66906299, compound

Product 1

HCID 66906152HCID 66906152, compound

Procedure

To 255 mg of 4-({[3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]carbonyl}oxy)benzoic 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, and the residue was then dissolved in THF. Diisopropylether was added dropwise thereto, and the precipitate was isolated by filtration. This was dried under reduced pressure at 50° C. to obtain 159 mg of 4-({[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]carbonyl}oxy)benzoic acid hydrochloride as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was then dissolved in THF
  3. additionDiisopropylether was added dropwise
  4. customthe precipitate was isolated by filtration
  5. customThis was dried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-240410543d74407db31572bd2370f70d
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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