Potassium Hydroxide → 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole

HRID 843756Notes

Reaction equation

HRID 843756 reaction equation
[OH-].[K+].[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2)([O-:5])=[O:4].[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1>CO>[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[C:19]1[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH:18]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 225235-NitroindoleHCID 740491-Methyl-4-piperidone

Product 1

HCID 113343733-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indoleYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 10.38 gm (185 mMol) potassium hydroxide in 200 mL methanol were added 10.0 gm (61.7 mMol) 5-nitro-1H-indole followed by 13.96 gm (123 mMol) 1-methyl-4-piperidone. The mixture was heated to reflux for 4 days under a nitrogen atmosphere. The reaction mixture was then allowed to cool to ambient and the solid which formed filtered and washed with methanol. This solid was dried under vacuum at 50° C. The combined filtrates were then concentrated under reduced pressure and the residue subjected to flash chromatography, eluting with 92.5:7.5 dichloromethane:methanol. Fractions shown to contain product were combined and concentrated under reduced pressure. This solid was combined with that isolated directly from the reaction mixture to give 13.79 gm (87%) 5-nitro-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 days under a nitrogen atmosphere
  3. temperatureto cool to ambient and the solid which
  4. customformed
  5. filtrationfiltered
  6. washwashed with methanol
  7. customThis solid was dried under vacuum at 50° C
  8. concentrationThe combined filtrates were then concentrated under reduced pressure
  9. washeluting with 92.5:7.5 dichloromethane
  10. concentrationconcentrated under reduced pressure
  11. customthat isolated directly from the reaction mixture

Sources & evidence

ORD record
ord-1554f6da8d594290b7b9ae7e7fef0a48
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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