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

HRID 2396499Notes

Reaction equation

HRID 2396499 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-5ef0fc615ed047b9baf1921a30cb120c
Source dataset
uspto-grants-1996_02
Patent number
US05492919

Reaction notes

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