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

HRID 641868Notes

Reaction equation

HRID 641868 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>[CH3:15][N:16]1[CH2:17][CH:18]=[C:19]([C:9]2[C:8]3[C:12](=[CH:13][CH:14]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=3)[NH:11][CH:10]=2)[CH2:20][CH2:21]1

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 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
72 °C

Procedure

A solution of KOH (12 g, 213.21 mmol) in methanol (100 mL) was added to 5-nitro-1H-indole (15 g, 92.04 mmol) in a 250 mL flask. 1-methylpiperidin-4-one (13.7 g, 120.46 mmol) was then added dropwise with stirring, while cooling the reaction to 20° C. The resulting solution was stirred for 4 hours, while the temperature was maintained at 72° C. The reaction mixture was then cooled to 15° C., and the product was precipitated by the addition of water (100 mL). Filtration, followed by recrystallization of the residue from ethanol afforded 11 g (46%) of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole as a yellow solid.

Workup

  1. temperaturewhile cooling
  2. customthe reaction to 20° C
  3. stirringThe resulting solution was stirred for 4 hours, while the temperature
  4. temperatureThe reaction mixture was then cooled to 15° C.
  5. customthe product was precipitated by the addition of water (100 mL)
  6. filtrationFiltration
  7. customfollowed by recrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-c84dac3f5b80461a86a108e4e808c80e
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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