1-benzyl-4-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]piperidin-4-ol → 4-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]piperidin-4-ol

HRID 2383015Notes

Reaction equation

HRID 2383015 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:15]([N:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]2[CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:16])([OH:14])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[CH:27]1([CH:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:25][CH2:26][N:17]2[C:15]([C:11]2([OH:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:16])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 1

HCID 593965611-benzyl-4-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]piperidin-4-ol

Product 1

HCID 593964104-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]piperidin-4-olYield 88.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

1-benzyl-4-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]piperidin-4-ol (220 mg) was dissolved in MeOH (12 mL), and 20% palladium hydroxide-supported activated carbon (360 mg) was added thereto, followed by stirring under a hydrogen atmosphere, at room temperature and normal pressure, for 15 hours. Thereafter, the catalyst was separated through celite. The solvent was evaporated to obtain 4-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]piperidin-4-ol (154 mg).

Workup

  1. additionwas added
  2. customThereafter, the catalyst was separated through celite
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8883bac642cf4bc68aff489c7a6ff4c4
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

Loading…