Formic Acid → 80836-03-9

HRID 1241880Notes

Reaction equation

HRID 1241880 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[C:18]([CH2:20]C)[CH:17]=[C:16]([CH2:22]C)[CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)=O>O.CCO.[Pd]>[CH3:20][C:18]1[CH:19]=[C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:15]=[C:16]([CH3:22])[CH:17]=1

Participants

6

Reactant 2

HCID 284Formic AcidHCID 21936938HCID 21936938, compound

Product 1

HCID 2193695780836-03-9Yield 83.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.24 g of 10% Pd on activated carbon were suspended in 15 mL of water, then a solution of 4.4 g (15.86 mmol) of 1-benzyl-4-(3,5-diethylphenyl)-1,2,3,6-tetrahydropyridine in 60 mL of EtOH was added followed by 1 mL of formic acid The resulting mixture was hydrogenated at 45 p.s.i. in a Parr apparatus for 6 h, then the catalyst was filtered off and the solvent was removed in vacuo. The resulting residue was taken up in water, basified with conc. NH4OH solution and extracted with CH2Cl2. The organic phase was dried and the solvent was removed in vacuo, yielding 2.5 g of the title compound, which was used without further purification.

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe solvent was removed in vacuo
  3. extractionextracted with CH2Cl2
  4. customThe organic phase was dried
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d264e0998ecc41f6af29b39c27da9be8
Source dataset
uspto-grants-2006_10
Patent number
US07115633B2

Reaction notes

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