1,4-Cyclohexanedione → SS-3227

HRID 2354028Notes

Reaction equation

HRID 2354028 reaction equation
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:16]=[CH:15][C:7]([O: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>C(O)C.[C].[Pd]>[OH:25][C:22]1[CH:23]=[CH:24][C:19]([N:12]2[CH2:11][CH2:10][CH:9]([O:8][C:7]3[CH:15]=[CH:16][C:4]([O:3][C:2]([F:1])([F:17])[F:18])=[CH:5][CH:6]=3)[CH2:14][CH2:13]2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 125111,4-CyclohexanedioneHCID 161154394-[4-(Trifluoromethoxy)phenoxy]piperidine

Product 1

HCID 11653258SS-3227Yield 89.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

261 mg of 4-(4-trifluoromethoxyphenoxy)piperidine, 224 mg of 1,4-cyclohexanedione and 4 mg of 10% palladium-carbon were heated in ethanol and reacted at 70° C. to 80° C. for 9 hours. After the completion of the reaction, the resultant was separated by silica gel column chromatography (n-hexane:ethyl acetate=3:1) and 315 mg of 1-(4-hydroxyphenyl)-4-(4-trifluoromethoxyphenoxy)piperidine was obtained (yield 89%).

Workup

  1. customreacted at 70° C. to 80° C. for 9 hours
  2. customAfter the completion of the reaction
  3. customthe resultant was separated by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f9df210fb59f4c119e3d972a10caa7f3
Source dataset
uspto-grants-2010_07
Patent number
US07750156B2

Reaction notes

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