Sodium hydride → 3-(1-Acetylpiperidyl)-5-(1-methyl-1H-indol-3-yl) tetrazole

HRID 2396498Notes

Reaction equation

HRID 2396498 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[NH:15][N:14]=[N: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:14]1[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]=[N:13]1)(=[O:21])[CH3:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 108221371-(Bromoacetyl)piperidine2×HCID 1784801415-(1-Methyl-1H-indol-3-yl)tetrazole

Product 1

HCID 189874193-(1-Acetylpiperidyl)-5-(1-methyl-1H-indol-3-yl) tetrazoleYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

5-(1-Methyl-1H-indol-3-yl)tetrazole (0.080 g, 0.402 mmol) was dissolved in dry THF (5 ml) and treated with sodium hydride (80%) (0.014 g, 0.441 mmol). When effervescence had ceased, 1-(bromoacetyl)piperidine (Bull. Soc. Chim. France 1964 5, 1063) (0.093 g, 0.422 mmol) in dry THF (2 ml) was added. After 1 h, a further amound of 1-(bromoacetyl)piperidine (0.047 g, 0.211 mmol) in dry THF (1 ml) was added. After a further 2 h, the reaction mixture was evaporated under reduced pressure to give a brown solid which was partitioned between CHCl3 and water. The organic layer was washed with NaHCO3 solution, and the combined aqueous layers were extracted with CHCl3. The combined organic layers were then dried (Na2SO4) and evaporated to give an off white foam which was dried in vacuo and then purified by silica-gel chromatography (pentane: EtOAc 1:1 as eluant) to give the title compound (D3 ) as a white solid (0.080 g, 61%)

Workup

  1. waitAfter a further 2 h
  2. customthe reaction mixture was evaporated under reduced pressure
  3. customto give a brown solid which
  4. customwas partitioned between CHCl3 and water
  5. washThe organic layer was washed with NaHCO3 solution
  6. extractionthe combined aqueous layers were extracted with CHCl3
  7. dry with materialThe combined organic layers were then dried (Na2SO4)
  8. customevaporated
  9. customto give an off white foam which
  10. customwas dried in vacuo
  11. custompurified by silica-gel chromatography (pentane: EtOAc 1:1 as eluant)

Sources & evidence

ORD record
ord-254fb4863b684414ae552f5c733e1831
Source dataset
uspto-grants-1996_02
Patent number
US05492919

Reaction notes

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