HCID 23141976, compound → 4-[4-Methyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]-1-propylpiperidine hydrochloride

HRID 2218905Notes

Reaction equation

HRID 2218905 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH3:17])[CH2:13][CH:14]=2)=[C:5]([CH:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[CH:4]=1>CO.[Pd]>[ClH:1].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH3:17])[CH2:13][CH2:14]2)=[C:5]([CH:18]2[CH2:19][C:20]([CH3:27])([CH3:26])[CH2:21][C:22]([CH3:24])([CH3:25])[CH2:23]2)[CH:4]=1

Participants

4

Reactant 1

HCID 23141976HCID 23141976, compound

Product 1

HCID 231418464-[4-Methyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]-1-propylpiperidine hydrochlorideYield 31.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[4-methyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]-1-propyl-1,2,3,6-tetrahydropyridine hydrochloride (50 mg, 0.13 mmol) produced in Example (104g) in methanol (10 mL) was added 10% palladium on carbon (50 mg, wet), followed by stirring for 2 hours at atmospheric pressure and room temperature under a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the obtained 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 16 mg of the title compound as a light yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe obtained 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-794ac4fa6bc3456d879b0166d1665593
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Reaction notes

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