1,4-Cyclohexanedione → SS-3227

HRID 2354027Notes

Reaction equation

HRID 2354027 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>[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

4

Reactant 2

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

Product 1

HCID 11653258SS-3227Yield 43.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

261 mg of 4-(4-trifluoromethoxyphenoxy)piperidine and 224 mg of 1,4-cyclohexanedione were heated under reflux in 5 ml of ethanol and reacted for 7 hours. After concentrating the reaction mixture under reduced pressure, the resultant was separated by silica gel column chromatography (n-hexane:ethyl acetate=3:1) and 154.9 mg of 1-(4-hydroxyphenyl)-4-(4-trifluoromethoxyphenoxy)piperidine was obtained (yield 43.8%).

Workup

  1. customreacted for 7 hours
  2. concentrationAfter concentrating the reaction mixture under reduced pressure
  3. customthe resultant was separated by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-aa7d2389db274cffb495e44e394fa6c5
Source dataset
uspto-grants-2010_07
Patent number
US07750156B2

Reaction notes

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