5-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole → 5-bromo-3-(1-methylpiperidin-4-yl)-1H-indole

HRID 277996Notes

Reaction equation

HRID 277996 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][N:14]([CH3:17])[CH2:15][CH:16]=1.[H][H]>O1CCCC1.[Pt]=O>[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][N:14]([CH3:17])[CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 149732085-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 157453445-bromo-3-(1-methylpiperidin-4-yl)-1H-indoleYield 73.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (44.6 g, 153 mmol) in 1.95 L tetrahydrofuran was added 9.0 gm platinum oxide. The reaction mixture was hydrogenated with an initial hydrogen pressure of 60 p.s.i. at ambient temperature for 24 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was recrystallized from acetonitrile to give 32.6 gm (73.7%) of the title compound as a white solid. MS(m/e): 293(M+). EA calculated for C14H17N2Br: C, 57.32; H, 5.96; N, 9.69. Found: C, 57.35; H, 5.84; N, 9.55.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d0670eca38e348ab870950efc55e6ade
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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