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

HRID 1936706Notes

Reaction equation

HRID 1936706 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=3)[NH:10][CH:9]=2)=[CH:4][CH2:3]1>[Pd].CO.CN(C=O)C>[NH2:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

5

Reactant 1

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

Product 1

HCID 118312203-(1-Methylpiperidin-4-yl)-1h-indol-5-amineYield 64.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole (D1, 2.00 g, 7.8 mmole) and 10% palladium on carbon (0.25 g) in methanol (50 ml) and DMF (50 ml) was shaken under an atmosphere of hydrogen at 50 psi/344.8 KPa for 18 hours. The mixture was filtered and evaporated to dryness. The residue was partitioned between dichloromethane (75 ml) and water (30 ml). The organic phase was separated, washed with brine, dried (Na2SO4) and evaporated to dryness. Trituration of the residue with diethyl ether afforded the title compound as pale brown solid (1.15 g).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness
  3. customThe residue was partitioned between dichloromethane (75 ml) and water (30 ml)
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-81d7388f57be4785a67b665e1e13763c
Source dataset
uspto-grants-2002_05
Patent number
US06391891B1

Reaction notes

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