1,4-Cyclohexanedione → HCID 70873346, compound

HRID 2172194Notes

Reaction equation

HRID 2172194 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[C:16]1(=O)[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1>[Pd].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 125111,4-CyclohexanedioneHCID 37320424-(3,4-Dichlorophenoxy)piperidine

Product 1

HCID 70873346HCID 70873346, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

10% palladium on carbon (350 mg) was added to an ethanol solution (50 ml) of 4-(3,4-dichlorophenoxy)piperidine (7.1 g) and 1,4-cyclohexanedione (6.47 g), and the mixture was stirred at 50 to 60° C. for 5 hours. After being cooled to room temperature, the catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, 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=9:1→3:1) to afford the title compound as a pale brown powder (5.2 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. customthe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed 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=9:1→3:1)

Sources & evidence

ORD record
ord-822f3477d8f94f88800a621ba63096a9
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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