1,4-Dioxane hydrochloride → HCID 66906098, compound

HRID 1691729Notes

Reaction equation

HRID 1691729 reaction equation
C(OC([N:8]([CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:34]([Cl:35])=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][N:27]=2)[CH2:22][CH:21]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH3:10])=O)(C)(C)C.Cl.O1CCOCC1>>[ClH:35].[Cl:35][C:34]1[C:26]([N:23]2[CH2:24][CH2:25][CH:20]([CH2:19][NH:8][C@@H:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[CH3:10])[CH:21]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:22]2)=[N:27][CH:28]=[C:29]([CH:33]=1)[C:30]([OH:32])=[O:31]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66906175HCID 66906175, compound

Product 1

HCID 66906098HCID 66906098, compound

Procedure

To 142 mg of the crude product of 6-[4-({(tert-butoxycarbonyl)[(1R)-1-(3-methoxyphenyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-5-chloronicotinic 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 was added ethanol and ethyl acetate, followed by heating under reflux, and then being left to be cooled to room temperature. Then, the precipitate was collected by filtration, and dried under reduced pressure to obtain 78 mg of 5-chloro-6-[4-({[(1R)-1-(3-methoxyphenyl)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 was added ethanol and ethyl acetate
  3. temperatureby heating
  4. temperatureunder reflux
  5. waitbeing left
  6. temperatureto be cooled to room temperature
  7. filtrationThen, the precipitate was collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-295849f4dbb4410a81daa03369d467b8
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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