2,5-Dimethoxytetrahydrofuran → 4-(Pyrrole-1-yl)-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide

HRID 2514

Reaktionsgleichung

Reaktionsgleichung von HRID 2514
[NH2:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([N:8]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25](=[O:33])[C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:21][CH2:20]2)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.CO[CH:38]1[CH2:42][CH2:41][CH:40](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([C:6]([N:8]([CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25](=[O:33])[C:26]4[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=4)[CH2:21][CH2:20]3)[C:9]3[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)=[O:7])=[CH:34][CH:35]=2)[CH:38]=[CH:42][CH:41]=[CH:40]1

Komponenten

4

Edukt 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 196899144-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide

Produkt 1

HCID 196898944-(Pyrrole-1-yl)-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamideAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide (237.0 mg, 0.50 mmol) was dissolved in acetic acid (5.0 ml), and the solution was mixed with 2,5-dimethoxytetrahydrofuran (0.065 ml, 0.50 mmol) and heated for 1 hour under reflux. After cooling, acetic acid was distilled off under a reduced pressure, the residue was dissolved in ethyl acetate, and the organic layer was washed with water and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was distilled off under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=1:4) to obtain 217.0 mg (82,7%) of the title compound in a colorless amorphous form.

Aufarbeitung

  1. temperatureheated for 1 hour
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. distillationacetic acid was distilled off under a reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washthe organic layer was washed with water and saturated brine
  7. dry with materialdried on anhydrous sodium sulfate
  8. distillationThereafter, the solvent was distilled off under a reduced pressure
  9. customthe resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=1:4)

Quellen und Nachweise

ORD-Eintrag
ord-af152361a976447c83199ce000045ab8
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728835

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