Dimethylformamide → HCID 68309050, compound

HRID 2171711Notes

Reaction equation

HRID 2171711 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:17]=[CH:18][C:19](=[O:22])[NH:20][CH:21]=2)[CH2:12][CH2:11]1.[CH3:23]N(C=O)C.C(=O)([O-])[O-].[K+].[K+].CI>C(Cl)(Cl)Cl.O>[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:17]=[CH:18][C:19](=[O:22])[N:20]([CH3:23])[CH:21]=2)[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 68309041HCID 68309041, compound

Product 1

HCID 68309050HCID 68309050, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

5-{4-[2-Fluoro-3-(hydroxymethyl)phenyl]piperazin-1-yl}pyridin-2(1H)-one (352 mg) and DMF (10 ml) were mixed, and potassium carbonate (240 mg) and methyl iodide (200 mg) were added thereto, followed by stirring at 60° C. overnight. Methyl iodide (49 mg) and potassium carbonate (48.1 mg) were added thereto, followed by stirring at 60° C. for 4 hours. The reaction mixture was cooled to room temperature, and water and CHCl3 were added thereto at 0° C. The organic layer was washed with water and saturated brine, and then dried over Na2SO4, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain 5-{4-[2-fluoro-3-(hydroxymethyl)phenyl]piperazin-1-yl}-1-methylpyridin-2(1H)-one (256 mg).

Workup

  1. stirringby stirring at 60° C. for 4 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customat 0° C
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-2da2962d2a3d4f0bb1f7a38db950eecc
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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