1,4-Dioxane hydrochloride → HCID 66906082, compound

HRID 1691721Notes

Reaction equation

HRID 1691721 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][C:32]=2[Cl:40])=[O:29])[CH2:24][CH:23]1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=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.Cl.O1CCOCC1>>[ClH:40].[Cl:40][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:31]=1[NH:30][C:28]([N:25]1[CH2:26][CH2:27][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])[CH:23]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:24]1)=[O:29])[C:35]([OH:37])=[O:36]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66906065HCID 66906065, compound

Product 1

HCID 66906082HCID 66906082, compound

Procedure

To 302 mg of the crude product of 4-({[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]carbonyl}amino)-3-chlorobenzoic 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 then added isopropanol, followed by heating under reflux. The mixture was cooled to room temperature, and the precipitate was then isolated by filtration, and dried under reduced pressure to obtain 147 mg of 3-chloro-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. temperatureby heating
  3. temperatureunder reflux
  4. temperatureThe mixture was cooled to room temperature
  5. customthe precipitate was then isolated by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-10de8aeb091046f28f81dc007dce7962
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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