5-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole → 5-fluoro-3-(piperidin-4-yl)-1H-indole

HRID 440936Notes

Reaction equation

HRID 440936 reaction equation
[F: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[CH2:16][CH2:15][NH:14][CH2:13][CH:12]=1.[H][H]>C(O)C.[Pd]>[F: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[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 113449595-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 117699295-fluoro-3-(piperidin-4-yl)-1H-indoleYield 76.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 10.75 gm (50 mMol) 5-fluoro-3-[1,2,5,6-tetrahydro-4-pyridyl]-1H-indole in 500 mL ethanol were added 2.0 gm 5% palladium on carbon and the reaction mixture hydrogenated at ambient temperature for 18 hours at an initial hydrogen pressure of 60 p.s.i. The reaction mixture was then filtered through a pad of celite and the filtrate concentrated under reduced pressure to give all off-white solid. The solid was recrystallized from methanol to give 8.31 gm (76.2%) of the title compound as a colorless solid. m.p.=229°-230° C.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto give all off-white solid
  4. customThe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-1ca887b1ef1141a5a4cb56c7c1d0235a
Source dataset
uspto-grants-1996_05
Patent number
US05521197

Reaction notes

Loading…