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

HRID 2357439Notes

Reaction equation

HRID 2357439 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>CO.[Pd].[C]>[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

4

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 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

3-(1-benzyl-1,2,5,6-tetrahydropyridine-3-yl)-1H-indole (430 mg, 1.48 mmole) was dissolved in methanol (30 ml) under argon. Pd/carbon (43 mg, 10%) was added and the reaction mixture was hydrogenated for 16 hours at 2 bar. The reaction mixture was worked up by filtering the solution through silica gel and washing with methanol (10×10 ml). The filtrate was concentrated by evaporation and dried. 3-piperidine-3-yl-1H-indole was obtained as a yellow oil in a yield of 233 g (79%).

Workup

  1. filtrationby filtering the solution through silica gel
  2. washwashing with methanol (10×10 ml)
  3. concentrationThe filtrate was concentrated by evaporation
  4. customdried

Sources & evidence

ORD record
ord-290d724ce5a746c48f97565f5c112889
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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