1H-Indol-5-amine, 3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)- → 3-(1-Methylpiperidin-4-yl)-1h-indol-5-amine

HRID 725962Notes

Reaction equation

HRID 725962 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]2[C:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH:16]=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]=[C:5]2[CH:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]1

Participants

5

Reactant 1

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

Product 1

HCID 118312203-(1-Methylpiperidin-4-yl)-1h-indol-5-amine

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-dbc998b214d84346801f744f10d3e7d0
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Reaction notes

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