Triethylamine → 4-[4-[Bis(4-fluorophenyl)amino]butyl]-2-piperazinecarboxamide

HRID 1494628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1494628
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH:22]1[C:27]([NH2:29])=[O:28].C(N(CC)CC)C>COCCO>[F:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2][N:24]2[CH2:25][CH2:26][NH:21][CH:22]([C:27]([NH2:29])=[O:28])[CH2:23]2)=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 3019914Piperazine-2-carboxamideHCID 14722551N-(4-chlorobutyl)-4-fluoro-N-(4-fluorophenyl)benzenamine

Produkt 1

HCID 147225524-[4-[Bis(4-fluorophenyl)amino]butyl]-2-piperazinecarboxamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80192-MethoxyethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 17.7 parts of N-(4-chlorbutyl)-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).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. extractionThe product was extracted twice with dichloromethane
  3. washThe combined extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol
  9. customThe pure fraction was collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from a mixture of 2,2'-oxybispropane and acetonitrile (80:20 by volume)
  12. filtrationThe product was filtered off
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-62de9e2112c94b0a837d17b222a53077
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05026853

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