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

HRID 254195노트

반응식

HRID 254195 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-0ae5a948bf3d4c89b1a664427823b482
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875605B2

반응 노트

불러오는 중…