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

HRID 392751

反応式

HRID 392751 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-287c7b5be3434c31b74c0207113ae0ee
出典データセット
uspto-grants-2004_10
特許番号
US06803362B2

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