Reaktion #4121

Reaktionsgleichung

N-[2-(5-bromo-1-indolinyl)phenyl]phenylcarbamate

N-methylpiperazine

→

product

Ausbeute 90.0%

N-[2-(5-bromo-1-indolinyl)phenyl]-4-methyl-1-piperazinecarboxamide

Ausbeute 90.0%

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe ether was evaporated
2. 2
   FiltrationThe mixture was filtered through a silica gel column (150 g)
3. 3
   Waschenthe column was washed with 2% methanol-dichloromethane solution (2 l)
4. 4
   SonstigeThe solvent was evaporated
5. 5
   SonstigeThe residue was purified by flash chromatography on a silica gel column (150 g, 230-400 mesh)
6. 6
   Wascheneluted with 1% methanol/dichloromethane (4 l), 1.5% methanol/dichloromethane (2 l), and 2% methanol/dichloromethane
7. 7
   workup.ADDITIONThe fractions containing the desired material
8. 8
   Sonstigewere collected
9. 9
   Sonstigeevaporated

Vorschrift

A solution of N-[2-(5-bromo-1-indolinyl)phenyl]phenylcarbamate (11.5 g, 28.5 mmoles), N-methylpiperazine (15 ml) and ether (50 ml) was stirred at room temperature for 2 hours. The ether was evaporated. The mixture was filtered through a silica gel column (150 g), packed with dichloromethaane, and the column was washed with 2% methanol-dichloromethane solution (2 l). The solvent was evaporated. The residue was purified by flash chromatography on a silica gel column (150 g, 230-400 mesh), eluted with 1% methanol/dichloromethane (4 l), 1.5% methanol/dichloromethane (2 l), and 2% methanol/dichloromethane. The fractions containing the desired material were collected and evaporated to give 10.9 g (90%) of product. Crystallization from chloroform and hexane afforded the analytical sample, mp 108°-110° C.

Quelle