1-Methylpiperazine → HCID 22010655, compound

HRID 323160Notes

Reaction equation

HRID 323160 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:48]=[CH:47][C:20]([C:21]([N:23]([CH3:46])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]([O:39]C4C=CC=CC=4)=O)=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:49][N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:46])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]([N:53]4[CH2:54][CH2:55][N:50]([CH3:49])[CH2:51][CH2:52]4)=[O:39])=[O:22])=[CH:47][CH:48]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 22010872HCID 22010872, compound

Product 1

HCID 22010655HCID 22010655, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-phenoxycarbonylaminopentyloxy)phenyl]benzamide (290 mg) in N,N-dimethylformamide (15 ml) was added 1-methylpiperazine (271 mg) at ambient temperature. The reaction mixture was stirred at 80° C. for 10 hours. The reaction mixture was cooled and extracted with ethyl acetate and washed with saturated sodium hydrogen carbonate and brine. The organic solution was dried over sodium sulfate. The solvent was removed by evaporation and subjected to silica gel column chromatography (SiO2; 30 g, 5% methanol in chloroform) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[5-(4-methylpiperazin-1-carbonylamino)pentyloxy]phenyl]benzamide (190 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate and brine
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-0e94d22493fb4be4a746d2d960776626
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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