Potassium Carbonate → Methyl 2-methoxy-4-(4-methylpiperazin-1-yl)benzoate

HRID 1186632Notes

Reaction equation

HRID 1186632 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11](F)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CS(C)=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([N:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]2)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 10241478Methyl 4-fluoro-2-methoxybenzoate

Product 1

HCID 66996253Methyl 2-methoxy-4-(4-methylpiperazin-1-yl)benzoateYield 66.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 2-methoxy-4-fluoro-benzoate (1.6 gr, 9.7 mmol), K2CO3 (1.3 gr, 9.7 mmol) and N-methyl piperazine (1.3 mL, 11.7 mmol) were heated at 100° C. in DMSO (5 mL) for 20 hours. Reaction mixture was diluted with DCM and washed with water. Organic phase was dried over sodium sulfate and evaporated to dryness. Column chromatography purification on silica gel using dichloromethane/methanol 95:5 as the eluant, afforded 1.7 g (yield 66%) of the title compound.

Workup

  1. customReaction mixture
  2. washwashed with water
  3. dry with materialOrganic phase was dried over sodium sulfate
  4. customevaporated to dryness
  5. customColumn chromatography purification on silica gel

Sources & evidence

ORD record
ord-4520751d330b4f69963a0ab915a824e1
Source dataset
uspto-grants-2014_03
Patent number
US08673893B2

Reaction notes

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