Water → HCID 68310301, compound

HRID 1021306Notes

Reaction equation

HRID 1021306 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][NH:19][C:18](=[O:22])[CH:17]=2)[CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][O:32][CH3:33].O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)(Cl)Cl>[F:1][C:2]1[C:3]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH2:30][CH2:31][O:32][CH3:33])[CH:17]=3)[CH2:12][CH2:11]2)=[CH:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 68309869HCID 68309869, compound

Product 1

HCID 68310301HCID 68310301, compoundYield 29.1%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-{4-[2-Fluoro-3-(hydroxymethyl)phenyl]piperazin-1-yl}pyridin-2(1H)-one (300 mg) was suspended in DMF (7.5 ml), and potassium carbonate (273 mg), 2-bromoethylmethyl ether (275 mg), and tetrabutylammonium iodide (37 mg) were added thereto, followed by stirring at 60° C. overnight. Water and CHCl3 were added to the reaction mixture, and the organic layer was washed with saturated brine and then dried over Na2SO4. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (MeOH/CHCl3) to obtain (2-fluoro-3-{4-[2-(2-methoxyethoxy)pyridin-4-yl]piperazin-1-yl}phenyl)methanol (104 mg).

Workup

  1. washthe organic layer was washed with saturated brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (MeOH/CHCl3)

Sources & evidence

ORD record
ord-1eb1d74780d14abd822982991e78c6b9
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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