Piperidine → HCID 118432100, compound

HRID 2207904Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][C:10](=O)[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:4][N:3]=1.Cl.[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[NH:28][NH2:29].N1CCCCC1>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[N:28]([C:22]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=3[F:20])[N:29]=[C:10]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH2:9]2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

1-(2-Bromo-pyridin-4-yl)-4,4,5,5,5-pentafluoro-pent-1-en-3-one (2.9 g, 8.9 mmol) prepared in Step 3, 2,4-difluorophenylhydrazine hydrochloride (2.4 g, 8.9 mmol), and piperidine (1.8 mL, 17.8 mmol) were added to ethanol (88.8 mL). The reaction mixture was stirred at 90° 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=1/3) to give 1.8 g of the titled compound as a yellow liquid.

Workup

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

Sources & evidence

ORD record: ord-94cf2ebaa2774980a265ac51be96c199
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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