HCID 22495591, compound → HCID 69745264, compound

HRID 1815840Notes

Reaction equation

HRID 1815840 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[O:21][CH:20]=[CH:19][C:18]=3[CH:17]=[C:16]([F:23])[CH:15]=2)[CH:10]([CH3:24])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)C>[CH3:24][C@H:10]1[C@@H:11]([C:14]2[C:22]3[O:21][CH:20]=[CH:19][C:18]=3[CH:17]=[C:16]([F:23])[CH:15]=2)[CH2:12][CH2:13][NH:8][CH2:9]1.[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]3=[CH:20][O:21][CH:22]=[CH:18][C:17]3=[CH:16][CH:15]=2)[CH:10]([CH3:24])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 22495591HCID 22495591, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 59012639HCID 59012639, compoundYield 33%HCID 69745264HCID 69745264, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A slurry of 0.80 gm 10% palladium on carbon in 100 mL ethanol was stirred under a hydrogen atmosphere. A solution of 4.23 gm (13.2 mMol) 1-benzyl-3-methyl-4-(5-fluorobenzofur-7-yl)-1,2,3,6-tetrahydropyridine in 100 mL ethanol was added and the mixture stirred under the hydrogen atmosphere for about 16 hours. The reaction mixture was filtered through a celite pad and the filter cake was washed with ethanol. The combined filtrates were concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography, eluting with a gradient of dichloromethane containing from 0-6% methanol, and then with 9:1:0.1 dichloromethane:methanol:ammonium hydroxide. Fractions containing product were combined and concentrated under reduced pressure to provide 1.0 gm (33%) cis-3-methyl-4-(5-fluorobenzofur-7-yl)piperidine and 1.75 gm (40%) 1-benzyl-3-methyl-4-(5-benzofur-7-yl)piperidine.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washthe filter cake was washed with ethanol
  3. concentrationThe combined filtrates were concentrated under reduced pressure
  4. washeluting with a gradient of dichloromethane containing from 0-6% methanol
  5. additionFractions containing product
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a8778bc4b3146b38c596de8e61250a1
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

Loading…