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

HRID 1884830Notes

Reaction equation

HRID 1884830 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-tetrahydro-pyridin-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-27a9fee34e864da4b43bcc7471fcd9a3
Source dataset
uspto-grants-2004_07
Patent number
US06767912B2

Reaction notes

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