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

HRID 2268768Notes

Reaction equation

HRID 2268768 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=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[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]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) were mixed under nitrogen with 6-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (20 g, 0.0926 mol) in ethanol (187.5 ml) and glacial acetic acid (62.5 ml). The reaction mixture was then hydrogenated at 60 psi until the reaction was complete by tlc. The catalyst was removed by fitration and the solvent evaporated in vacuo to give a yellow solid which was dried at 60° C. in vacuo (EP 722941).

Workup

  1. customThe catalyst was removed by fitration
  2. customthe solvent evaporated in vacuo
  3. customto give a yellow solid which
  4. customwas dried at 60° C. in vacuo (EP 722941)

Sources & evidence

ORD record
ord-551d65e8e7ed4354abfae5fa31c8ca0b
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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