1-Methyl-1,4-cyclohexadiene → 1-(3-Hydroxyphenyl)-4-(4-morpholinyl)-1-butanone

HRID 1986389Notes

Reaction equation

HRID 1986389 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]CC3C=CC=CC=3)[CH:13]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CC1CC=CCC=1>CCO.[Pd]>[OH:18][C:14]1[CH:13]=[C:12]([C:10](=[O:11])[CH2:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 780061-Methyl-1,4-cyclohexadieneHCID 688741424-(4-Morpholinyl)-1-{3-[(phenylmethyl)oxy]phenyl}-1-butanone

Product 1

HCID 688754221-(3-Hydroxyphenyl)-4-(4-morpholinyl)-1-butanoneYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product of Step 3 (352 mg, 1.04 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 concentrate to afford the title compound as a white solid (255 mg, 99%). MS (ES+) m/e 250 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-cffcbc2994174a69bf516a05463aa714
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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