3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole → 3-(4-Piperidinyl)-1H-indole

HRID 2357433Notes

Reaction equation

HRID 2357433 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1>CO.[Pd].[C]>[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 7022353-(4-Piperidinyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

3-(1,2,3,6-tetrahydropyridine-4-yl)-1H-indole (3 g, 16.5 mmole) was dissolved in methanol (50 ml) under argon. Pd/carbon (150 mg, 5%) was added and the reaction mixture was hydrogenated for 8 hours at 2 bar. The reaction mixture 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. 3-piperidine-4-yl-1H-indole was obtained in a yield of 3.3 g (100%) with an m.p. of 190°-192° 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-1e32c2de28714735a14a6ca1fc943ed1
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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