Potassium Carbonate → 1-(2-[Bis(4-fluorophenyl)methoxy]ethyl)-4-[4-oxo-4-(2-thienyl)butyl]piperazine

HRID 1197512

Reaktionsgleichung

Reaktionsgleichung von HRID 1197512
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.Cl[CH2:26][CH2:27][CH2:28][C:29]([C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)=[O:30].C(=O)([O-])[O-].[K+].[K+]>CC(CC(C)C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:26][CH2:27][CH2:28][C:29](=[O:30])[C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)[CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1235114-Chloro-1-(2-thienyl)butan-1-oneHCID 99740131-[2-[Bis(4-fluorophenyl)methoxy]ethyl]piperazine

Produkt 1

HCID 100740681-(2-[Bis(4-fluorophenyl)methoxy]ethyl)-4-[4-oxo-4-(2-thienyl)butyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 1.67 g (0.005 mol) 1-(2-[bis(4-fluorophenyl)-methoxy]ethyl)piperazine, (U.S. Pat. No. 1545094), 1.89 g (0.010 mol) 3-chloropropyl-2-thienyl ketone, 1.52 g (0.011 mol) potassium carbonate and 30 ml methylisobutyl ketone was stirred and heated to reflux for 45 h. The reaction mixture was then evaporated in vacuo. The residue was redissolved in dichloromethane (1 00 ml) and washed twice with water (100 ml). The organic layer was then separated and dried with sodium sulfate. Evaporation in vacuo left a brown syrup. This was redissolved in dry ether and precipitated as the dihydrochloride with gaseous hydrogen chloride. The precipitate was collected by filtration and recrystallized from isopropanol. White crystals, m.p. 185°-88° C. (0.98 g=35%).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 45 h
  3. customThe reaction mixture was then evaporated in vacuo
  4. dissolutionThe residue was redissolved in dichloromethane (1 00 ml)
  5. washwashed twice with water (100 ml)
  6. customThe organic layer was then separated
  7. dry with materialdried with sodium sulfate
  8. customEvaporation in vacuo
  9. waitleft a brown syrup
  10. dissolutionThis was redissolved in dry ether
  11. customprecipitated as the dihydrochloride with gaseous hydrogen chloride
  12. filtrationThe precipitate was collected by filtration
  13. customrecrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-5d52bbf3b12e44bfb5300f2ecded92f4
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05276035

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