Reaktion #479933

Reaktionsgleichung

methyl-piperazine

5-Bromo-benzofuran-2-carboxylic acid

carbonyldiimidazole

→

title compound

Ausbeute 53.3%

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

Ausbeute 53.3%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
4. 4
   Waschenwashed with saturated sodium bicarbonate solution, whereupon the organic portion
5. 5
   Sonstigewas separated out
6. 6
   Trocknendried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   SonstigeThe solvent was evaporated
9. 9
   Sonstigethe residue was purified via silica gel chromatography (5% 2 M ammonina in methanol/dichloromethane)

Vorschrift

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.

Quelle