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

HRID 1936705Notes

Reaction equation

HRID 1936705 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[CH3:13][N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.C[O-].[Na+]>CO>[CH3:13][N:14]1[CH2:19][CH2:18][C:17]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[NH:9][CH:8]=2)=[CH:16][CH2:15]1

Participants

5

Reactant 3

HCID 225235-NitroindoleHCID 740491-Methyl-4-piperidoneHCID 10942334Sodium Methoxide

Product 1

HCID 113343733-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indoleYield 65.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of 5-nitro-1H-indole (1.94 g, 12 mmole), 1-methylpiperidin-4-one (2.71 g, 24 mmole) and sodium methoxide (3.89 g, 72 mmole) in dry methanol (100 ml) was heated to reflux for 30 h. The cooled mixture was concentrated by evaporation and neutralized with 2M HCl acid. The resultant yellow precipitate was collected by filtration, washed with water and dried in vacuo to afford the title compound as a yellow powder (2.01 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 h
  3. concentrationThe cooled mixture was concentrated by evaporation
  4. filtrationThe resultant yellow precipitate was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-dd5540f47a0940d98d7b31fa7eb9178e
Source dataset
uspto-grants-2002_05
Patent number
US06391891B1

Reaction notes

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