1-Methylpiperazine → (5-Bromo-benzofuran-2-yl)-(4-methyl-piperazin-1-yl)-methanone

HRID 392751

반응식

HRID 392751 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=O)=[CH:7][C:6]=2[CH:13]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([N:30]3[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]3)=[O:12])=[CH:7][C:6]=2[CH:13]=1

참가 물질

5

반응물 3

HCID 531671-MethylpiperazineHCID 682631,1'-CarbonyldiimidazoleHCID 7352475-Bromo-2-benzofurancarboxylic acid

생성물 1

HCID 9966975(5-Bromo-benzofuran-2-yl)-(4-methyl-piperazin-1-yl)-methanone수율 53.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-Bromo-benzofuran-2-carboxylic acid (0.346 g) in THF (7 mL) was treated with carbonyldiimidazole (0.214 g) and stirred at ambient temperature for 2 h whereupon methyl-piperazine (0.129 g) was added. The mixture was stirred at ambient temperature for 18 h and then concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate solution, whereupon the organic portion was separated out, dried over sodium sulfate and filtered. The solvent was evaporated, and the residue was purified via silica gel chromatography (5% 2 M ammonina in methanol/dichloromethane) to afford the title compound (0.222 g). 1H NMR (400 MHz, CDCl3): δ 7.75 (d, J=1.9 Hz, 1H), 7.45 (dd, J=8.8, 1.9 Hz, 1H), 7.37 (d, J=8.8 Hz, 1H), 3.83 (br s, 4H), 2.48 (t, J=4.8 Hz, 4H), 2.33 (s, 3H). 13C NMR (400 MHz, CDCl3) δ 159.4, 153.4, 150.3, 129.6, 129.0, 124.9, 116.8, 113.5, 111.3, 55.3, 54.9, 46.8, 46.1, 42.9.

후처리

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with saturated sodium bicarbonate solution, whereupon the organic portion
  5. customwas separated out
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was evaporated
  9. customthe residue was purified via silica gel chromatography (5% 2 M ammonina in methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-287c7b5be3434c31b74c0207113ae0ee
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803362B2

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