N,N-Diethylpiperazine-1-carboxamide → HCID 13690989, Verbindung

HRID 2290782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2290782
Cl[CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1.[CH2:23]([N:25]([CH2:34][CH3:35])[C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27])[CH3:24]>CN(C=O)C>[CH2:34]([N:25]([CH2:23][CH3:24])[C:26]([N:28]1[CH2:29][CH2:30][N:31]([CH2:2][C:3]2[N:7]=[C:6]([CH:8]([CH3:22])[C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:11]([F:21])[CH:10]=3)[O:5][N:4]=2)[CH2:32][CH2:33]1)=[O:27])[CH3:35]

Komponenten

4

Edukt 2

HCID 67067N,N-Diethylpiperazine-1-carboxamideHCID 136909413-Chloromethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

Produkt 1

HCID 13690989HCID 13690989, VerbindungAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2.14 g of 3-chloromethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole, 2.54 g of N,N-diethyl-1-piperazine carboxamide and 15 ml of dry DMF was heated at 100° C. for 2 hours. After cooling, the reaction mixture was poured into ice-water and extracted with diethyl ether. The organic phase was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed over silica gel using chloroform-methanol (50:1, v/v) to yield 2.43 g of 3-[4-(N,N-diethylcarbamoyl)piperazinomethyl]-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole as a light brown oil. To a solution of this product in ethanol was added equal mole of ethanolic hydrogen chloride and the mixture was concentrated to dryness under reduced pressure. Recrystallization of the residue from ethanol-diethyl ether gave colorless crystals, m.p. 181°-182° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-94a6bd1a287e4b93b036c74d0620cede
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04618617

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