5-Methoxyindole → 5-Methoxy-3-(piperidin-4-yl)-1H-indole

HRID 457841Notes

Reaction equation

HRID 457841 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[NH:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1>[Pt](=O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:15]1[CH2:16][CH2:17][NH:12][CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 138725-MethoxyindoleHCID 337214-Piperidone

Product 1

HCID 432245-Methoxy-3-(piperidin-4-yl)-1H-indoleYield 74%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

This compound was prepared following the procedure described in example 1 (parts A and B) starting with 5.9 g (40 mmol) of 5-methoxyindol and 15.5 g (100 mmol) of 4-piperidone. In this case the hydrogenation took place for 24 hours at 30 psi and the catalyst used was platinum (IV) oxide. 6.8 g (74% of yield) of 5-methoxy-3-piperidin-4-yl-1H-indole were obtained.

Workup

  1. customThis compound was prepared
  2. customfor 24 hours

Sources & evidence

ORD record
ord-ec2ee785a40c45e881fc369aa5a5b091
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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