3-(1-benzyl-1,2,5,6-tetrahydropyridine-3-yl)-1H-indole → 3-(Piperidin-3-YL)-1H-indole

HRID 1070571Notes

Reaction equation

HRID 1070571 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]=[C:10]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:9]1)C1C=CC=CC=1>[Pd].C(O)=O.CO>[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:9]1

Participants

5

Reactant 1

HCID 158138493-(1-benzyl-1,2,5,6-tetrahydropyridine-3-yl)-1H-indole

Product 1

HCID 153894433-(Piperidin-3-YL)-1H-indole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of the 3-(1-benzyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole obtained in Example 28 and 10% palladium on carbon in a mixture of formic acid and methanol is stirred at room temperature for 3 days and filtered through celite. The celite is washed with methanol. The filtrates are combined and concentrated in vacuo to afford the title product, identified by HPLC and mass spectral analyses.

Workup

  1. filtrationfiltered through celite
  2. washThe celite is washed with methanol
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b97ffb06b57448b295827501b7262b07
Source dataset
uspto-grants-2005_06
Patent number
US06903112B2

Reaction notes

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