1-Methylpiperazine → 2-(2-Benzo[1,3]dioxol-5-yl-acetylamino)-6-fluoro-4-(4-methyl-piperazin-1-yl)-benzoic acid methyl ester

HRID 2039547Notes

Reaction equation

HRID 2039547 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[C:9]([F:10])=[CH:8][C:7](F)=[CH:6][C:5]=1[NH:12][C:13](=[O:24])[CH2:14][C:15]1[CH:23]=[CH:22][C:18]2[O:19][CH2:20][O:21][C:17]=2[CH:16]=1.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>CS(C)=O>[CH3:1][O:2][C:3](=[O:25])[C:4]1[C:9]([F:10])=[CH:8][C:7]([N:30]2[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]2)=[CH:6][C:5]=1[NH:12][C:13](=[O:24])[CH2:14][C:15]1[CH:23]=[CH:22][C:18]2[O:19][CH2:20][O:21][C:17]=2[CH:16]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 670432172-(2-Benzo[1,3]dioxol-5-yl-acetylamino)-4,6-difluoro-benzoic acid methyl ester

Product 1

HCID 670428092-(2-Benzo[1,3]dioxol-5-yl-acetylamino)-6-fluoro-4-(4-methyl-piperazin-1-yl)-benzoic acid methyl esterYield 25%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(2-benzo[1,3]dioxol-5-yl-acetylamino)-4,6-difluoro-benzoic acid methyl ester (0.50 g, 1.43 mmol) in dimethylsulfoxide (8 mL) was added N-methylpiperazine (0.20 mL, 2.86 mmol). The reaction was stirred at 80° C. for 3 h then cooled at room temperature. The solid precipitated was filtered and washed with a mixture H2O/EtOH 1/1, to provide after drying the title compound (0.15 g, 25% yield).

Workup

  1. temperaturethen cooled at room temperature
  2. customThe solid precipitated
  3. filtrationwas filtered
  4. washwashed with a mixture H2O/EtOH 1/1
  5. customto provide

Sources & evidence

ORD record
ord-085f88f62e3748c78074f94fd364faa8
Source dataset
uspto-grants-2013_11
Patent number
US08580783B2

Reaction notes

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