Sodium hydride → HCID 19959229, Verbindung

HRID 54560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 54560
[H-].[Na+].[NH2:3][C:4]1[N:8]=[C:7]([CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)[O:6][N:5]=1.Cl.[CH2:18]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][C:32](Cl)=[O:33])[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][C:32]([NH:3][C:4]2[N:8]=[C:7]([CH:9]3[CH:14]4[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]4)[CH2:10]3)[O:6][N:5]=2)=[O:33])[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 1951113-(3-Amino-1,2,4-oxadiazole-5-yl)-quinuclidineHCID 19959133(1-Benzylpiperidin-4-yl)acetyl chloride hydrochloride

Produkt 1

HCID 19959229HCID 19959229, VerbindungAusbeute 26,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (0.4 g) in N,N-dimethylformamide was added 3-amino-5-(quinuclidin-3-yl)-1,2,4-oxadiazole (0.2 g) at 0° C. and the mixture was stirred for 1 hour. To the mixture was added (1-benzylpiperidin-4-yl)acetyl chloride hydrochloride (2.53 g) during 30 minutes at 0° C. After stirred for additional 1 hour. The mixture was quenched with water and extracted with ethyl acetate. The extract was washed with water, brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on alumina with chloroform to give 3-{(1-benzylpiperidin-4-yl)acetylamino}-5-(quinuclidin-3-yl)-1,2,4-oxadiazole (0.11 g).

Aufarbeitung

  1. stirringAfter stirred for additional 1 hour
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on alumina with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-48e48bb72ee04b2f81a39faadc7903ce
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622976

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