1,4-Dioxane hydrochloride → HCID 66905939, compound

HRID 1691748Notes

Reaction equation

HRID 1691748 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[C:36]([F:37])=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][N:29]=2)[CH2:24][CH:23]1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=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:44].O1CCOCC1>>[ClH:44].[F:37][C:36]1[C:28]([N:25]2[CH2:26][CH2:27][CH:22]([CH2:21][NH:8][C@@H:9]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)[CH3:10])[CH:23]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:24]2)=[N:29][CH:30]=[C:31]([CH:35]=1)[C:32]([OH:34])=[O:33]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66905964HCID 66905964, compound

Product 1

HCID 66905939HCID 66905939, compound

Procedure

To 187 mg of the crude product of 6-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-5-fluoronicotinic acid was added 2.0 mL of a 4 M hydrogen chloride/1,4-dioxane solution. After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure, and to the obtained residue were added isopropanol and ethyl acetate, followed by heating under reflux, and then being left to be cooled to room temperature. The precipitate was collected by filtration, and dried under reduced pressure to obtain 106 mg of 5-fluoro-6-[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]nicotinic acid hydrochloride as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionto the obtained residue were added isopropanol and ethyl acetate
  3. temperatureby heating
  4. temperatureunder reflux
  5. waitbeing left
  6. temperatureto be cooled to room temperature
  7. filtrationThe precipitate was collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-942a9142d6c542a5ba75319a66e35e75
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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