Methanol → HCID 22729249, compound

HRID 1507192Notes

Reaction equation

HRID 1507192 reaction equation
F[C:2]1[CH:3]=[C:4]([C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[H][H].[CH3:18]O>[Pd]>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)=[C:3]([CH3:18])[CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 28374495HCID 28374495, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22729249HCID 22729249, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 4-(3-fluoro-4-methoxyphenyl)-1,2,3,6-tetrahydropyridine (300 mg, 1.4 mmol) in MeOH (10 mL) was added Pd/C (154 mg). Hydrogen gas was introduced under balloon pressure and the reaction mixture was stirred vigorously for 12 h. The reaction mixture was filtered through a glass fiber filter cartridge, and the filter pad was washed with ethyl acetate. The combined organic layers were evaporated under reduced pressure to give 4-(4-methoxy-2-methylphenyl)piperidine (500 mg, 87% yield). LC/MS (Method P) RT=0.60 min. (M+H)+=210.1.

Workup

  1. filtrationThe reaction mixture was filtered through a glass fiber
  2. filtrationfilter cartridge
  3. washthe filter pad was washed with ethyl acetate
  4. customThe combined organic layers were evaporated under reduced pressure

Sources & evidence

ORD record
ord-cd19ff8e5e314abc9e6f56432544c4fc
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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