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

HRID 1276334Notes

Reaction equation

HRID 1276334 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH:12]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1>C(O)C.C(O)(=O)C.[Pt]=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 110530726-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 110960776-fluoro-3-(piperidin-4-yl)-1H-indole

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolvent2×

Procedure

A mixture of platinum oxide (1.0 g) in ethanol (37.5 ml) and glacial acetic acid (12.5 ml) was treated under nitrogen with 4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydropyridine (20 g, 92.6 mmol) in ethanol (187.5 ml) and glacial acetic acid (62.5 ml). The nitrogen was evacuated and hydrogen was admitted. The reaction mixture was then hydrogenated at 60 psi until the reaction was complete by tlc. The catalyst was removed by filtration and the solvent evaporated in vacuo to give a yellow solid which after drying at 60C in vacuo weighed.

Workup

  1. customThe nitrogen was evacuated
  2. customThe catalyst was removed by filtration
  3. customthe solvent evaporated in vacuo
  4. customto give a yellow solid which
  5. dry with materialafter drying at 60C in vacuo

Sources & evidence

ORD record
ord-fe0f5607edb74e7d82503f42d6b13059
Source dataset
uspto-grants-2000_12
Patent number
US06166040

Reaction notes

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