Dimethyl Sulfoxide → Methyl 2-methyl-4-(4-methylpiperazin-1-yl)benzoate

HRID 1803866Notes

Reaction equation

HRID 1803866 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][C:5]=1[CH3:11].[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+].CS(C)=O>C(Cl)Cl>[CH3:11][C:5]1[CH:6]=[C:7]([N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]2)[CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 2782181Methyl 4-fluoro-2-methylbenzoate

Product 1

HCID 54298739Methyl 2-methyl-4-(4-methylpiperazin-1-yl)benzoateYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

In a cylindrical quartz tube were placed 4-fluoro-2-methyl-benzoic acid methyl ester (1.2 g, 7.14 mmol), N-methylpiperazine (0.95 ml, 8.5 mmol), K2CO3 (990 mg, 7.14 mmol) and DMSO (4 ml). The reaction was heated for 20 hours at 110° C. until HPLC revealed the disappearance of the starting-material. DCM (15 ml) was added and the solution was washed twice with water and the organic phase was dried over anhydrous Na2SO4. The crude was purified by flash chromatography (DCM/MeOH 95:5) affording the desired compound (670 mg, 38%).

Workup

  1. customIn a cylindrical quartz tube were placed
  2. washthe solution was washed twice with water
  3. dry with materialthe organic phase was dried over anhydrous Na2SO4
  4. customThe crude was purified by flash chromatography (DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-42af34958a74446e9a2789e26fd8a153
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

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