Formic Acid → HCID 24904197, compound

HRID 2263511Notes

Reaction equation

HRID 2263511 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=1.C(O)=O>C(O)(C)C.[Pd]>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 23149940HCID 23149940, compound

Product 1

HCID 24904197HCID 24904197, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 4-(2,3-difluorophenyl)-1,2,3,6-tetrahydropyridine (2.4 g, 12.3 mmol), palladium on active carbon (0.5 g) and formic acid (2.4 ml) in isopropanol (50 ml) was hydrogenated at 50 psi for 6 h under hydrogen gas. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated and evaporated to dryness. Aqueous sodium carbonate (10%, 50 ml) was added. The aqueous phase was extracted with ethylacetate (3×60 ml) and the combined organic phases was dried (MgSO4), filtered and evaporated to dryness. Yield: 2.11 g. MS m/z (rel. intensity, 70 eV) 197 (M+, bp), 196 (53), 140 (11), 127 (10), 114 (6).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customevaporated to dryness
  4. additionAqueous sodium carbonate (10%, 50 ml) was added
  5. extractionThe aqueous phase was extracted with ethylacetate (3×60 ml)
  6. dry with materialthe combined organic phases was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-c2eb7d7a181a490aa45c3843969c9514
Source dataset
uspto-grants-2010_12
Patent number
US07851629B2

Reaction notes

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