3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole → 3-(1-Methylpiperidin-4-yl)-1h-indol-5-amine

HRID 2109625Notes

Reaction equation

HRID 2109625 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1>CO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 1

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

Product 1

HCID 118312203-(1-Methylpiperidin-4-yl)-1h-indol-5-amineYield 66.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(1-Methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-5-nitro-1H-indole (2.7 g, Step A) was dissolved in 50 mL MeOH, the mixture was bubbled with H2 for 10 min. 10% Pd/C (150 mg) was added and the mixture was stirred under H2 overnight. The mixture was then filtered through Celite® and concentrated in vacuo to afford a yellow oil (1.6 g). MS: 230 (M+1). Calc'd. for C14H19N3-229.3.

Workup

  1. customthe mixture was bubbled with H2 for 10 min
  2. addition10% Pd/C (150 mg) was added
  3. filtrationThe mixture was then filtered through Celite®
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e74dd93827ad4bc7bdd71bfed95e849c
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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