1-Methyl-1,4-cyclohexadiene → 3-[3-(4-Methyl-1-piperazinyl)-3-oxopropyl]phenol

HRID 1986392Notes

Reaction equation

HRID 1986392 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:18])/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)[CH2:4][CH2:3]1.CC1CC=CCC=1>CCO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8](=[O:18])[CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 780061-Methyl-1,4-cyclohexadieneHCID 68874178HCID 68874178, compound

Product 1

HCID 688716113-[3-(4-Methyl-1-piperazinyl)-3-oxopropyl]phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution the product of Example 17, Step 1 (300 mg, 1.22 mmol) in EtOH (15 mL), was added 10% palladium on carbon (50 mg), followed with 1-methyl-1,4-cyclohexadiene (1.5 mL). This suspension was then heated to reflux for 45 min. The reaction mixture was filtered and concentrated to afford the title compound, as a white solid (291 mg, 96%). MS (ES+) m/e 249 [M+H]+.

Workup

  1. temperatureThis suspension was then heated
  2. temperatureto reflux for 45 min
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c1e2b2701a9c4fafb764a307587141f4
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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