4-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride → 4-(4-Fluoro-phenyl)-piperidine hydrochloride

HRID 2085400Notes

Reaction equation

HRID 2085400 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)=[CH:5][CH:4]=1>CO.[Pd]>[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 1977474-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Product 1

HCID 218981684-(4-Fluoro-phenyl)-piperidine hydrochlorideYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (10 g) in methanol (200 mL) was added 10% palladium on charcoal (0.5 g) and the mixture was hydrogenated at 50 psi for 3 h. The catalyst was removed by filtration and solvent was evaporated, leaving the product (10.0 g) as a white powder, which was used in the next step without purification. The product appeared to be pure based on 1H NMR and TLC analysis. 1H NMR δ 1.95-2.03 (br d, 2H), 2.14-2.29 (m, 2H), 2.70-2.80 (m, 1H), 2.91-3.07 (br q, 2H), 3.60-3.64 (br d, 2H), 6.96-7.03 (m, 2H), 7.19-7.22 (m, 2H), 9.60 (br s, 1H), 9.71 (br s, 1H).

Workup

  1. customThe catalyst was removed by filtration and solvent
  2. customwas evaporated

Sources & evidence

ORD record
ord-aa9aa618a7c64ba2a33a0583294c2a4e
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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