Methane → HCID 67239030, compound

HRID 880501Notes

Reaction equation

HRID 880501 reaction equation
[F:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.OC1C=CC=C2C=1N=CC=C2.C(=O)([O-])[O-].[K+].[K+].[OH-].[NH4+].C>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:8]=[C:7]([N:19]2[CH2:20][CH2:21][N:16]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=3)[CH2:17][CH2:18]2)[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

9

Reactant 6

HCID 297MethaneHCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 944591-(2-Pyridyl)piperazineHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 67239030HCID 67239030, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
142.5 °C

Procedure

2-Fluoro-4-iodoaniline (750 mg, 3.16 mmol) was added to a suspension of 2-pyridyl-piperazine (568 mg, 3.48 mmol), 8-hydroxyquinoline (68 mg, 0.47 mmol) and potassium carbonate (660 mg, 4.74 mmol) in dimethylsulfoxide (5 mL) under an inert atmosphere. Cuprous iodide (94 mg, 0.47 mmol) was added and the reaction mixture was heated at 140-145° C. for 16 h. The reaction mixture was allowed to cool to ambient temperature and poured into a mixture of ammonium hydroxide, ethyl acetate and charcoal and stirred for 30 min. The organic layer was separated and the aqueous layer extracted with ethyl acetate (2×75 mL). The combined organic layers were washed with brine (100 mL), dried over sodium sulphate and concentrated to dryness in vacuo. The crude product was purified by column chromatography with silica gel (100-200 mesh) using 13% ethyl acetate in petroleum ether as eluent to afford 2-fluoro-4-[4-(2-pyridyl)piperazin-1-yl]aniline (220 mg, 26%) as an orange semi-solid.

Workup

  1. temperatureto cool to ambient temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with ethyl acetate (2×75 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness in vacuo
  7. customThe crude product was purified by column chromatography with silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-c353b9ae79294f47a82aa4ceb0b8cdfe
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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