Potassium Hydroxide → HCID 68602613, compound

HRID 641872Notes

Reaction equation

HRID 641872 reaction equation
[OH-].[K+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1)([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[CH2:21][CH2:20][CH:19]([C:10]2[C:9]3[C:13](=[CH:14][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=3)[NH:12][CH:11]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 785026-Nitro-1H-indole

Product 1

HCID 68602613HCID 68602613, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

KOH (3.96 g, 70.71 mmol) was added to a solution of 6-nitro-1H-indole (5 g, 30.86 mmol) in methanol (50 mL). 1-methylpiperidin-4-one (4.53 g, 40.09 mmol) was then added, and the resulting solution was stirred for 6 hours at 90° C. After cooling, the mixture was concentrated and the residue was recrystallized from ethanol (20 mL) to afford 3.0 g (36%) of 3-(1-methylpiperidin-4-yl)-6-nitro-1H-indole as a yellow powder.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. customthe residue was recrystallized from ethanol (20 mL)

Sources & evidence

ORD record
ord-6aaecbfb93bf4e45aa1073b5982e2a75
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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