Water → N-(1-methoxycarbonylpiperidin-4-yl)-N'-(4-fluorophenyl)urea

HRID 49787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 49787
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[O:9])[CH2:3][CH2:2]1.N1C=CC=CC=1.Cl[C:25]([O:27][CH3:28])=[O:26].O>O1CCCC1.C(OCC)(=O)C>[CH3:28][O:27][C:25]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[O:9])[CH2:3][CH2:2]1)=[O:26]

Komponenten

7

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 167815363-(4-fluorophenyl)-1-(piperidin-4-yl)urea

Produkt 1

HCID 9796177N-(1-methoxycarbonylpiperidin-4-yl)-N'-(4-fluorophenyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-(piperidin-4-yl)-N′-(4-fluorophenyl)urea (0.3 g) in tetrahydrofuran (4 ml) were added in turn pyridine (0.28 ml), methyl chloroformate (98 μl) and catalytic amount of N,N-dimethylaminopyridine at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 2 hours. The reaction mixture was taken up into a mixture of water and ethyl acetate. The separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate, and brine, and dried over magnesium sulfate. Evaporation under reduced pressure gave a residue, which was triturated with diisopropyl ether to give N-(1-methoxycarbonylpiperidin-4-yl)-N′-(4-fluorophenyl)urea (0.312 g).

Aufarbeitung

  1. washThe separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate, and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation under reduced pressure
  4. customgave a residue, which
  5. customwas triturated with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-54fccd73dcba46ffa30693578c68994e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710043B1

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