HCID 23141597, compound → HCID 23142612, compound

HRID 32268Notes

Reaction equation

HRID 32268 reaction equation
[ClH:1].[CH2:2]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[C:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]([CH3:28])([CH3:27])[CH:20]=2)[CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5]>CO.[Pd]>[ClH:1].[CH2:2]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[CH:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]([CH3:27])([CH3:28])[CH2:20]2)[CH2:10][CH2:11]1)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 1

HCID 23141597HCID 23141597, compound

Product 1

HCID 23142612HCID 23142612, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-butyl-4-[5-fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperidine hydrochloride (47 mg, 0.12 mmol) produced in Example (106h) in methanol (3 mL) was added 10% palladium on carbon (100 mg, wet), followed by stirring for 4 hours at atmospheric pressure and room temperature under a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. Hexane was added to the residue to produce a solid, which was then triturated by sonication. The solid was filtered and dried under reduced pressure to give 19 mg of the title compound as a light yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionHexane was added to the residue
  4. customto produce a solid, which
  5. customwas then triturated by sonication
  6. filtrationThe solid was filtered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-68b4036efe7a4df6a38bb1df88b5efdf
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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