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

HRID 1773429Notes

Reaction equation

HRID 1773429 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-c3ba68fc943e4f788c218c5ff4a73f5d
Source dataset
uspto-grants-2016_02
Patent number
US09255087B2

Reaction notes

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