1-Methylpiperazine → (1-Benzenesulfonyl-1H-indol-3-yl)-(4-methylpiperazin-1-yl)methanone

HRID 254195Notes

Reaction equation

HRID 254195 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19](O)=[O:20])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>ClCCl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]([N:32]3[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]3)=[O:20])=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 65578Oxalyl chlorideHCID 7364841-(phenylsulfonyl)-1H-indole-3-carboxylic acid

Product 1

HCID 11740685(1-Benzenesulfonyl-1H-indol-3-yl)-(4-methylpiperazin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Benzenesulfonylindole-3-carboxylic acid (3.01 g, 0.01 moles) was stirred with oxalyl chloride (1.309 g, 0.011 moles) in 20 mL dichloromethane at 0 to 25° C. for 3-4 hours. After completion of the reaction (T.L.C.), volatile substances were distilled off under the reduced pressure. The residue was taken in 20 mL dichloroethane and to this stirred solution, was added N-methylpiperazine (1.1 g, 0.011 moles). The reaction mixture was further stirred for next 3-5 hours till the reaction completes (TLC). Reaction mixture was diluted with dichloromethane 20 mL), washed with water, brine and saturated solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and the organic solvents were evaporated under vacuo. The product was purified using column chromatography on silica gel G stationary phase and suitable combinations of ethyl acetate and methanol in increasing gradient as the mobile phase. IR spectra (cm−1) 3140, 1621, 1552, 1451; Mass (m/z): 484 (M+H)+

Workup

  1. customAfter completion of the reaction (T.L.C.), volatile substances
  2. distillationwere distilled off under the reduced pressure
  3. customReaction mixture
  4. washwashed with water, brine and saturated solution of sodium bicarbonate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe organic solvents were evaporated under vacuo
  7. customThe product was purified
  8. temperaturein increasing gradient as the mobile phase

Sources & evidence

ORD record
ord-0ae5a948bf3d4c89b1a664427823b482
Source dataset
uspto-grants-2011_01
Patent number
US07875605B2

Reaction notes

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