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

HRID 32262Notes

Reaction equation

HRID 32262 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-86c9cf90851546da952ea9d0c2340e1f
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

Loading…