Pyridine → 4-Trifluoroacetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide

HRID 2518

Reaktionsgleichung

Reaktionsgleichung von HRID 2518
[NH2:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([N:8]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[F:40][C:41]([F:46])([F:45])[C:42](O)=[O:43].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:40][C:41]([F:46])([F:45])[C:42]([NH:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([N:8]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23](=[O:31])[C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[CH2:19][CH2:18]2)[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1)=[O:43]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 196900714-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide

Produkt 1

HCID 196899224-Trifluoroacetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamideAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (229.3 mg, 0.51 mmol) was dissolved in methylene chloride (2.0 ml) to which were subsequently added pyridine (0.05 ml, 0.62 mmol) and anhydrous trifluoroacetic acid (0.09 ml, 0.64 mmol) at 0° C. After 3 hours of stirring at 0° C. to room temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution and extracted with chloroform. The resulting organic layer was washed with saturated sodium chloride aqueous solution and water in that order, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to obtain 224.8 mg (81.2%) of the title compound in a light yellow powder form.

Aufarbeitung

  1. customat 0° C
  2. extractionextracted with chloroform
  3. washThe resulting organic layer was washed with saturated sodium chloride aqueous solution and water in that order
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThereafter, the solvent was removed by evaporation
  6. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-83156c93ebe44f9b836d2b41d4fbb6ea
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728835

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