Sodium hydride → 1-[1-Acetylpiperidyl]-3-(1-methyl-1H-indol-3-yl)-1,2,4-triazole

HRID 2396499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2396499
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[N:15]=[CH:14][NH:13][N:12]=2)=[CH:3]1.[H-].[Na+].Br[CH2:19][C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21]>C1COCC1>[C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[N:13]1[CH:14]=[N:15][C:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[N:12]1)(=[O:21])[CH3:19]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 108221371-(Bromoacetyl)piperidineHCID 178480138HCID 178480138, Verbindung

Produkt 1

HCID 543655421-[1-Acetylpiperidyl]-3-(1-methyl-1H-indol-3-yl)-1,2,4-triazoleAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3-(1-Methyl-1H-indol-3-yl)-1,2,4-triazole (0.190 g, 0.960 mmol) was dissolved with stirring in dry THF (5 ml) and was treated with sodium hydride (80%) (0.032 g, 1.05 mmol), followed by 1-(bromoacetyl)piperidine (Bull. Soc, Chim. Fr. 1964, 5, 1063-9) (0.232 g, 1.05 mmol) in dry THF (1 ml). After 4 h, the reaction mixture was evaporated under reduced pressure and partitioned between EtOAc and water. The organic layer was then dried (Na2SO4) and evaporated under reduced pressure to give a yellow oil, which was purified by silica-gel chromatography (EtOAc→EtOAc:MeOH 100:1 as eluant) to give the title compound (D5b) as a white solid (0.080 g, 26%).

Aufarbeitung

  1. customthe reaction mixture was evaporated under reduced pressure
  2. custompartitioned between EtOAc and water
  3. dry with materialThe organic layer was then dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customto give a yellow oil, which
  6. customwas purified by silica-gel chromatography (EtOAc→EtOAc:MeOH 100:1 as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-5ef0fc615ed047b9baf1921a30cb120c
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05492919

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