HCID 18797135, compound → 2-(Piperidin-4-yl)-1H-indole

HRID 1003587Notes

Reaction equation

HRID 1003587 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].C(O)C>[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 18797135HCID 18797135, compound

Product 1

HCID 133608972-(Piperidin-4-yl)-1H-indoleYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.521 gm (1.8 mMol) 2-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole and 0.1 gm 5% palladium on carbon were stirred together in ethanol under hydrogen (1 atm) for 48 hours. The reaction mixture was filtered through a bed of celite and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 20% methanol in dichloromethane containing a trace of ammonium hydroxide. Fractions containing product were combined and concentrated under reduced pressure to provide 0.107 gm (30%) 2-(piperidin-4-yl)-1H-indole as a light yellow solid. A portion of this material was treated with oxalic acid to provide the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through a bed of celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. washeluting with 20% methanol in dichloromethane containing a trace of ammonium hydroxide
  4. additionFractions containing product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1021d023561439e94388f1b4c1d7718
Source dataset
uspto-grants-2000_04
Patent number
US06046215

Reaction notes

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