1,4-Cyclohexanedione → HCID 67275119, compound

HRID 2172186Notes

Reaction equation

HRID 2172186 reaction equation
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1.[C:19]1(=O)[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1>[Pd].C(O)C>[F:18][C:2]([F:17])([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[CH2:11][CH2:10]2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 125111,4-CyclohexanedioneHCID 23081575HCID 23081575, compound

Product 1

HCID 67275119HCID 67275119, compoundYield 17.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

10% palladium on carbon (64 mg) was added to an ethanol solution (13 ml) of 4-(4-trifluoromethoxybenzyl)piperidine (1.28 g) and 1,4-cyclohexanedione (1.19 g), and the mixture was stirred at 70 to 80° C. for 8.5 hours. After being cooled to room temperature, the catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. After being dissolved in ethyl acetate, the residue was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. After being concentrated under reduced pressure, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→6:4) to afford the title compound as a black oil (305 mg).

Workup

  1. temperatureAfter being cooled to room temperature
  2. customthe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionAfter being dissolved in ethyl acetate
  5. washthe residue was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter being concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→6:4)

Sources & evidence

ORD record
ord-cf96a904f7bc4cee9e8328e307e9cf53
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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