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

HRID 725960Notes

Reaction equation

HRID 725960 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH:18]=1)([O-])=O.[H][H]>C(O)C.Cl.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]1[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]1

Participants

6

Reactant 2

HCID 113343733-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 118312203-(1-Methylpiperidin-4-yl)-1h-indol-5-amineYield 147.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 38.2 gm (145 mMol) 5-nitro-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 1.9 L ethanol and 30 mL 5N HCl were added 10.0 gm 5% palladium on carbon. The reaction mixture was hydrogenated at ambient for 18 hours with an initial hydrogen pressure of 60 p.s.i. The reaction mixture was filtered and then concentrated under reduced pressure. The residue was dissolved in methanol and the solution filtered. This filtrate was concentrated under reduced pressure and the residue redissolved in ethanol. The solution was concentrated to about 500 mL and product allowed to crystallize. The crystals were filtered to give 48.9 gm (95%) of the title compound as its dihydrochloride salt, ethanol solvate.

Workup

  1. customambient for 18 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in methanol
  5. filtrationthe solution filtered
  6. concentrationThis filtrate was concentrated under reduced pressure
  7. dissolutionthe residue redissolved in ethanol
  8. concentrationThe solution was concentrated to about 500 mL and product
  9. customto crystallize
  10. filtrationThe crystals were filtered

Sources & evidence

ORD record
ord-91a395353e6743afaf17d09ff006e21e
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Reaction notes

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