HCID 66582509, compound → HCID 66582589, compound

HRID 1972503Notes

Reaction equation

HRID 1972503 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12](CC2C=CC=CC=2)[CH2:11][CH2:10][N:9]1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.[Pd]>[CH2:1]([C@H:8]1[CH2:13][NH:12][CH2:11][CH2:10][N:9]1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66582509HCID 66582509, compound

Product 1

HCID 66582589HCID 66582589, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 100 mL round bottomed flask a mixture of 2-(4-((2S)-2,4-dibenzyl-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (355 mg, 0.781 mmol) and 10% Pd/C (83 mg) in EtOH (20 mL) was placed under a hydrogen atmosphere (1 atm) 16 h. The mixture was filtered through a pad of Celite® (diatomaceous earth) and then concentrated onto silica gel and purified via column chromatography (40 g, 0 to 10% MeOH in CH2Cl2) to give 2-(4-((2S)-2-benzyl-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (0.210 g).

Workup

  1. custom(1 atm) 16 h
  2. filtrationThe mixture was filtered through a pad of Celite® (diatomaceous earth)
  3. concentrationconcentrated onto silica gel
  4. custompurified via column chromatography (40 g, 0 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-59653e95d0ca4cb6af466b1fed295a42
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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