5-nitro-2-(pyridin-2-yl)-1H-indole → 2-(piperidin-2-yl)-1H-indol-5-amine

HRID 468384Notes

Reaction equation

HRID 468384 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH:7]2)([O-])=O>Cl.CO>[NH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[C:8]1[NH:9][C:10]2[C:6]([CH:7]=1)=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=2

Participants

3

Reactant 1

HCID 591293805-nitro-2-(pyridin-2-yl)-1H-indole

Product 1

HCID 591294712-(piperidin-2-yl)-1H-indol-5-amineYield 110.6%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

5-Nitro-2-(pyridin-2-yl)-1H-indole (1.0 g, 4.2 mmol) was added to HCl/MeOH (2 M, 50 mL). The reaction mixture was stirred at room temperature for 1 h and the solvent was evaporated under vacuum. PtO2 (200 mg) was added to a solution of the residue in MeOH (50 mL) and the reaction mixture was stirred under hydrogen atmosphere (1 atm) at room temperature for 2 h. The catalyst was filtered through a celite pad and the solvent was evaporated under vacuum to afford 2-(piperidin-2-yl)-1H-indol-5-amine (1.0 g), which was directly used in the next step.

Workup

  1. customthe solvent was evaporated under vacuum
  2. additionPtO2 (200 mg) was added to a solution of the residue in MeOH (50 mL)
  3. stirringthe reaction mixture was stirred under hydrogen atmosphere (1 atm) at room temperature for 2 h
  4. filtrationThe catalyst was filtered through a celite pad
  5. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-0f97acb3d4ff4885bc06424b7ff77a2e
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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