Sodium Hydroxide → 4-Ureido-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide

HRID 2512

Reaktionsgleichung

Reaktionsgleichung von HRID 2512
[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][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[O-:36][C:37]#[N:38].[K+].C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(O)(=O)C.O>[NH:1]([C:2]1[CH:3]=[CH:4][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:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[CH2:21][CH2:20]2)[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[O:7])=[CH:34][CH:35]=1)[C:37]([NH2:38])=[O:36]

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 11378442Potassium cyanateHCID 196898814-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide

Produkt 1

HCID 196898334-Ureido-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamideAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899381Acetic acid--water (1/1)Lösungsmittel

Versuchsvorschrift

4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (237.2 mg, 0.50 mmol) was dissolved in acetic acid-water (1:2, 1.8 ml) to which was subsequently added dropwise an aqueous solution (0.5 ml) of potassium cyanate (81.1 mg, 0.90 mmol) After 3 hours of stirring at room temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution, alkanized with 10% sodium hydroxide aqueous solution and then extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1) and recrystallized from ethyl acetate-ether to obtain 125.6 mg (48.4%) of the title compound in a colorless powder form.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe resulting organic layer was washed with water and saturated brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThereafter, the solvent was removed by evaporation
  5. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1)
  6. customrecrystallized from ethyl acetate-ether

Quellen und Nachweise

ORD-Eintrag
ord-1cf1796f970a4f61aff232d412aa105f
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728835

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