HCID 22495566, compound → HCID 22495668, compound

HRID 1815835Notes

Reaction equation

HRID 1815835 reaction equation
C(O)(=O)/C=C/C(O)=O.[CH3:9][CH:10]1[CH2:15][C:14]([C:16]2[C:24]3[O:23][CH:22]=[CH:21][C:20]=3[CH:19]=[C:18]([F:25])[CH:17]=2)=[CH:13][CH2:12][NH:11]1.C(O)(=O)/C=C/C(O)=O.CC1C=C(C2C3OC=CC=3C=C(F)C=2)CCN1>[Pd].C(O)C>[CH3:9][CH:10]1[CH2:15][CH:14]([C:16]2[C:24]3[O:23][CH:22]=[CH:21][C:20]=3[CH:19]=[C:18]([F:25])[CH:17]=2)[CH2:13][CH2:12][NH:11]1

Participants

5

Reactant 2

HCID 22495566HCID 22495566, compoundHCID 22495583HCID 22495583, compound

Product 1

HCID 22495668HCID 22495668, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.045 gm (0.13 mMol) 2-methyl-4-(5-fluorobenzofur-7-yl)-1,2,3,6-tetrahydropyridine fumarate and 2-methyl-4-(5-fluorobenzofur-7-yl)-1,2,5,6-tetrahydropyridine fumarate and 0.010 gm 10% palladium on carbon in 5 mL ethanol was hydrogenated at 1 atmosphere at room temperature for 5 hours. The reaction mixture was filtered through a pad of celite. The pad was rinsed with ethanol and the filtrate was concentrated under reduced pressure. The residue was subjected to ion exchange chromatography on an SCX column, eluting with methanol followed by 0.5N ammonia in methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 0.024 gm (79%) 2-methyl-4-(5-fluorobenzofur-7-yl)piperidine. This was dissolved in 5 mL ethanol and the solution was heated to reflux. To this solution were added 0.007 gm (0.06 mMol) fumaric acid. After mixing for about 5 minutes, the reaction mixture was diluted with diethyl ether. The mixture was concentrated under reduced pressure and the residue dried at 60° C. under vacuum for about 15 hours to provide 0.013 gm of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washThe pad was rinsed with ethanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washeluting with methanol
  5. additionFractions containing product
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0934f6a50c5542fe979bc298689f87fc
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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