4-(6-Fluoronaphth-2-yl)-1,2,5,6-tetrahydropyridine → 4-(6-Fluoronaphth-2-yl)piperidine

HRID 1760624Notes

Reaction equation

HRID 1760624 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH:13]=1)[CH:6]=[CH:5]2>C(O)C.[Pt]=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1)[CH:6]=[CH:5]2

Participants

4

Reactant 1

HCID 129927744-(6-Fluoronaphth-2-yl)-1,2,5,6-tetrahydropyridine

Product 1

HCID 129927764-(6-Fluoronaphth-2-yl)piperidineYield 82.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a mixture of 4-(6-fluoronaphth-2-yl)-1,2,5,6-tetrahydropyridine (0.691 g, 3.04 mmol) in ethanol (20 mL) was added platinum oxide (0.03 g). The mixture was hydrogenated at one atmosphere for 20 hours. The mixture was carefully filtered and evaporated to give 4-(6-fluoronaphth-2-yl)piperidine as a white amorphous solid (0.572 g, 82%). A small portion was converted to the oxalate salt to give the title compound. FDMS m/e=230 (M++1 of free base).

Workup

  1. filtrationThe mixture was carefully filtered
  2. customevaporated

Sources & evidence

ORD record
ord-8220e2ea32dd4d43ad616bebdbd2124e
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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