1H-Indol-5-amine, 3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)- → 5-Aminoindole

HRID 843759Notes

Reaction equation

HRID 843759 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2C1CCN(C)CC=1>CO.[Pd].CCCCCC>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 1

HCID 111488671H-Indol-5-amine, 3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-

Product 1

HCID 788675-Aminoindole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To a solution of 11.3 gm (50 mMol) 5-amino-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 250 mL methanol were added 3.0 gm 5% palladium on carbon. The mixture was hydrogenated at room temperature under an initial hydrogen pressure of 60 p.s.i. for 18 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to give a dark gum which was slurried in hexane to give the title compound as a brown solid.

Workup

  1. customwas hydrogenated at room temperature under an initial hydrogen
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customto give a dark gum which

Sources & evidence

ORD record
ord-6bbc107c101846a59ed67dc8253f27e2
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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