5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole → 4-(5-chloro-[1H]-indol-3-yl)-piperidine

HRID 2357431Notes

Reaction equation

HRID 2357431 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1>CO.[Pd].[C]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 128313754-(5-chloro-[1H]-indol-3-yl)-piperidine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

5-chloro-3-(1,2,3,6-tetrahydropyridine-4-yl)-1H-indole (2 g, 9.25 mmole) was dissolved in methanol (50 ml) under argon. Pd/carbon (100 mg, 5%) was added and the reaction mixture was hydrogenated for 8 hours at 2 bar. The product was worked up by filtering the solution through silica gel and washing with methanol (10×20 ml). The filtrate was concentrated by evaporation and dried. 5-chloro-3-piperidine-4-yl-1H-indole was obtained in a yield of 2 g (100%) with an m.p. of 156°-158° C.

Workup

  1. filtrationby filtering the solution through silica gel
  2. washwashing with methanol (10×20 ml)
  3. concentrationThe filtrate was concentrated by evaporation
  4. customdried

Sources & evidence

ORD record
ord-d06039e8da5144a59418dbbca20ba181
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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