Piperidine → HCID 118432098, compound

HRID 2207965Notes

Reaction equation

HRID 2207965 reaction equation
[F:1][C:2]([F:25])([C:21]([F:24])([F:23])[F:22])[C:3](=O)[CH:4]=[CH:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1.Cl.[CH:27]1([NH:33][NH2:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.N1CCCCC1>C(O)C>[CH:27]1([N:33]2[CH:5]([C:6]3[CH:7]=[C:8]([C:12]4[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=4)[CH:9]=[CH:10][CH:11]=3)[CH2:4][C:3]([C:2]([F:25])([F:1])[C:21]([F:24])([F:23])[F:22])=[N:34]2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 207836Cyclohexylhydrazine hydrochlorideHCID 131735937HCID 131735937, compound

Product 1

HCID 118432098HCID 118432098, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

4,4,5,5,5-Pentafluoro-1-(4′-methylsulfanyl-biphenyl-3-yl)-pent-1-en-3-one (200.0 mg, 0.54 mmol) prepared in Step 3 of Preparation 4, cyclohexylhydrazine hydrochloride (98.0 mg, 0.59 mmol), and piperidine (107.0 uL, 1.08 mmol) were added to ethanol (5.0 mL). The reaction mixture was stirred at 100° C. for 18 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The reaction mixture was washed with distilled water, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/60) to give 10.0 mg of the titled compound as a yellow liquid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionethyl acetate was added
  3. washThe reaction mixture was washed with distilled water
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow liquid residue
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/60)

Sources & evidence

ORD record
ord-2d74f56d27b746faaf6b14d9db0ae9f5
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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