Piperidine → HCID 118431784, compound

HRID 2207871Notes

Reaction equation

HRID 2207871 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][C:10](=O)[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[N:6][CH:7]=1.Cl.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][NH2:28].N1CCCCC1>C(O)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]([CH:8]2[N:27]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[Cl:20])[N:28]=[C:10]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 4432872-Chlorophenylhydrazine hydrochlorideHCID 131735935HCID 131735935, compound

Product 1

HCID 118431784HCID 118431784, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

1-(5-Bromo-pyridin-2-yl)-4,4,5,5,5-pentafluoro-pent-1-en-3-one (936.0 mg, 2.8 mmol) prepared in Step 3, 2-chlorophenylhydrazine hydrochloride (508.0 mg, 2.8 mmol), and piperidine (560.0 uL, 5.7 mmol) were added to ethanol (28.4 mL). The reaction mixture was stirred at 60° C. for 2 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The 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=1/10) to give 450.0 mg of the titled compound as a yellow liquid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionethyl acetate was added
  3. washThe 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=1/10)

Sources & evidence

ORD record
ord-5228e41632d14356be67a32657fb41db
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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