Water → HCID 67509283, compound

HRID 623464Notes

Reaction equation

HRID 623464 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.Cl.[F:12][C:13]([F:17])([F:16])[CH2:14][NH2:15].O>CN1CCCC1=O>[F:12][C:13]([F:17])([F:16])[CH2:14][NH:15][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-one

Product 1

HCID 67509283HCID 67509283, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
230 °C

Procedure

A mixture of 1-(6-chloropyridin-3-yl)ethanone (1.0 g, 6.43 mmol) and 2,2,2-trifluoroethanamine hydrochloride (1.57 g, 11.8 mmol) in 1-methylpyrrolidin-2-one (10 mL) is stirred at 230° C. for 45 minutes under microwave irradiation. The reaction mixture is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (4:1 to 1:1) to give 490 mg (35% yield) of the title compound as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (4:1 to 1:1)

Sources & evidence

ORD record
ord-28ab58c62b194c9aa4bcb7b1da708d4c
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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