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Sodium Iodide → N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-methoxymethyl-N-(2-methoxyphenyl)benzamide

HRID 2468
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2468
[CH3:1][O:2][CH2:3][C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[O:9])=[CH:6][CH:5]=1.Cl.Cl[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH:28]([C:31](=[O:39])[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH2:27][CH2:26]1.[I-].[Na+].[H-].[Na+]>CN(C=O)C>[F:38][C:35]1[CH:34]=[CH:33][C:32]([C:31]([CH:28]2[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])[C:8](=[O:9])[C:7]3[CH:6]=[CH:5][C:4]([CH2:3][O:2][CH3:1])=[CH:20][CH:19]=3)[CH2:26][CH2:27]2)=[O:39])=[CH:37][CH:36]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 174450244-Methoxymethyl-N-(2-methoxyphenyl)benzamideHCID 675753381-(2-Chloroethyl)-4-(4-fluorobenzoyl)piperidine hydrochloride

Produkt 1

HCID 19689885N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-methoxymethyl-N-(2-methoxyphenyl)benzamideAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In an atmosphere of argon, 4-methoxymethyl-N-(2-methoxyphenyl)benzamide (126 mg, 0.464 mmol), 1-(2-chloroethyl)-4-(4-fluorobenzoyl)piperidine hydrochloride (157 mg, 0.511 mmol) and sodium iodide (154 mg, 1.02 mmol) were dissolved in DMF (3 ml) to which was subsequently added sodium hydride (40 mg, 60%, 1.0 mmol) at room temperature. After stirring at room temperature for 10 minutes and then at 60° C. for 3.5 hours, DMF was removed by evaporation. The resulting residue was diluted with water (10 ml) and extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and then dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by subjecting it to a silica gel column chromatography (methylene chloride:methanol=80:1-ethyl acetate) to obtain 128 mg (54.7%) of the title compound in the form of colorless oil.

Aufarbeitung

  1. customat room temperature
  2. waitat 60° C. for 3.5 hours
  3. customDMF was removed by evaporation
  4. additionThe resulting residue was diluted with water (10 ml)
  5. extractionextracted with ethyl acetate
  6. washthe organic layer was washed with water and saturated brine
  7. dry with materialdried on anhydrous sodium carbonate
  8. customThereafter, the solvent was removed by evaporation
  9. customthe resulting residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-1362f36b27ab4a15833b7044edb1e473
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05728835

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