Acetonitrile → ethyl N-[N-(4-cyanobenzoyl)carbamoyl]piperidin-4-yloxyacetate

HRID 1900913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900913
C(O)(=O)C.[NH:5]1[CH2:10][CH2:9][CH:8]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7][CH2:6]1.[C:18]([C:20]1[CH:30]=[CH:29][C:23]([C:24]([N:26]=[C:27]=[O:28])=[O:25])=[CH:22][CH:21]=1)#[N:19].C(#N)C>C(N(CC)CC)C>[C:18]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:26][C:27]([N:5]2[CH2:6][CH2:7][CH:8]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:10]2)=[O:28])=[O:25])=[CH:29][CH:30]=1)#[N:19]

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 149137394-Cyanobenzoyl isocyanateHCID 131719662Ethyl piperidin-4-yloxyacetate, acetate salt

Produkt 1

HCID 23369999ethyl N-[N-(4-cyanobenzoyl)carbamoyl]piperidin-4-yloxyacetateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

In a similar manner to Example 1, starting material step (a), the product from step (b) (1.7 g), 4-cyanobenzoyl isocyanate (1.1 g), acetonitrile (100 ml total) and triethylamine (2.1 ml) were stirred at ambient temperature overnight. The mixture was evaporated and the residue was purified by column chromatography on silica eluting with 5% ethanol/dichloromethane to give ethyl N-[N-(4-cyanobenzoyl)carbamoyl]piperidin-4-yloxyacetate (1.24 g) as a pale yellow oil: NMR Spectrum (DMSO-d6) 1.21 (3H, t), 1.50 (2H, m), 1.87 (2H, m), 3.20 (2H, m), 3.67 (3H, m), 4.12 (2H, q), 4.15 (2H, s), 7.97 (4H, s), 10.40 (1H, br s); Mass Spectrum m/Z 360 (M+H)+.

Aufarbeitung

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography on silica eluting with 5% ethanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-426687c57a754075954b9f49e75e6c70
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576334

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