Acetic Acid → HCID 57725142, compound

HRID 1016177Notes

Reaction equation

HRID 1016177 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH3:15])([CH3:14])[CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:4][CH:3]=1.C(O)(=O)C>CO.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH3:15])[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 57888772HCID 57888772, compound

Product 1

HCID 57725142HCID 57725142, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(4-fluorophenyl)-3,3-dimethyl-1,2,3,6-tetrahydropyridine (450 mg, 2.192 mmol), palladium hydroxide on carbon (308 mg, 2.192 mmol), and acetic acid (1.5 mL, 26.2 mmol) in methanol (10 mL) was degassed under nitrogen/vacuum, then hydrogenated at 50 psi for two days. The catalyst was removed by filtration and rinsed with methanol, and the filtrate was concentrated in vacuo to yield the title compound (442 mg, 2.132 mmol, 97% yield) as a pale yellow oil. MS (ESI+)=208.29, (M+H)+.

Workup

  1. customwas degassed under nitrogen/vacuum
  2. customThe catalyst was removed by filtration
  3. washrinsed with methanol
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b8b606b8c30144908c849c1e1828f3d1
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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