Reaktion #1160339

Reaktionsgleichung

N-(4-chlorobutyl)-4-fluoro-N-(4-fluorophenyl)benzenamine

2-piperazinecarboxamide

N,N-diethylethanamine

→

4-[4-[bis-(4-fluorophenyl)amino]butyl]-2-piperazinecarboxamide

Ausbeute 55.0%

Lösungsmittel

2-methoxyethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was evaporated
2. 2
   ExtraktionThe product was extracted twice with dichloromethane
3. 3
   WaschenThe combined extracts were washed with water
4. 4
   Sonstigedried
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by column chromatography over silica gel using
8. 8
   workup.ADDITIONa mixture of trichloromethane and methanol
9. 9
   SonstigeThe pure fraction was collected
10. 10
    Sonstigethe eluent was evaporated
11. 11
    SonstigeThe residue was crystallized from a mixture of 2,2'-oxybispropane and acetonitrile (80:20 by volume)
12. 12
    FiltrationThe product was filtered off
13. 13
    Sonstigedried

Vorschrift

A mixture of 17.7 parts of N-(4-chlorobutyl)-4-fluoro-N-(4-fluorophenyl)benzenamine. 23.3 parts of 2-piperazinecarboxamide, 17.6 parts of N,N-diethylethanamine and 300 parts of 2-methoxyethanol was stirred for 48 hours at 70° C. The reaction mixture was evaporated and the residue was taken up in water and a small amount of methanol. The product was extracted twice with dichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fraction was collected and the eluent was evaporated. The residue was crystallized from a mixture of 2,2'-oxybispropane and acetonitrile (80:20 by volume). The product was filtered off and dried, yielding 12.82 parts (55.0%) of 4-[4-[bis-(4-fluorophenyl)amino]butyl]-2-piperazinecarboxamide; mp. 67.4° C. (int. 28).

Quelle