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

HRID 481945Notes

Reaction equation

HRID 481945 reaction equation
[Br: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.[H][H]>[Pt].[Pt]=O.C(OC(=O)C)C.O1CCCC1>[Br: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

6

Reactant 2

HCID 27637245-Bromo-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 112429275-Bromo-3-(piperidin-4-yl)-1H-indoleYield 75.6%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

To a solution of 13.61 gm (49 mmol) 5-bromo 3-[1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole in 75 ml 2:1 tetrahydro-furan ethyl acetate were added 8.0 gm 3% sulfided platinum on carbon and 4.0 gm platinum oxide. The reaction mixture was hydrogenated with an initial hydrogen pressure of 60 p.s.i. at 40° C. for 18 hours and then at ambient temperature for 30 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to give 10.33 gm (75.6%) of the title compound as a light yellow solid.

Workup

  1. waitat ambient temperature for 30 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-3b7960c8df6a49329e071789304e5601
Source dataset
uspto-grants-1998_08
Patent number
US05792760

Reaction notes

Loading…