Piperidine → 5-Acetonyl-3-piperidinomethyl-1,2,4-oxadiazole

HRID 247110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 247110
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10]Cl)[N:6]=1)[C:2]([CH3:4])=[O:3].C(N(CC)CC)C.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C1COCC1>[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:6]=1)[C:2]([CH3:4])=[O:3]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 138247055-Acetonyl-3-chloromethyl-1,2,4-oxadiazole

Produkt 1

HCID 138247065-Acetonyl-3-piperidinomethyl-1,2,4-oxadiazoleAusbeute 56,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 15.0 g of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole in 50 ml of THF were added dropwise 17.4 g of triethylamine and subsequently 11.0 g of piperidine. The mixture was stirred at room temperature for 24 hours and then heated under reflux for 6 hours. After cooling, the precipitated material was removed by filtration and the filtrate was evaporated in vacuo. The residue was chromatographed on silica gel using chloroform-methanol (20:1, v/v) as eluent to give 10.9 g of 5-acetonyl-3-piperidinomethyl-1,2,4-oxadiazole as a colorless solid, m.p. 66°-67° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. customthe precipitated material was removed by filtration
  5. customthe filtrate was evaporated in vacuo
  6. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-424a10afc27f4ca58e6791c1a2642d37
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705786

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