HCID 57656776, compound → HCID 57656882, compound

HRID 603249Notes

Reaction equation

HRID 603249 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][C:15](=[CH:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:25][CH3:26])[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]>[Pd].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:13][CH2:14][CH:15]([CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:25][CH3:26])[CH2:20]3)[CH2:16][CH2:17]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 57656776HCID 57656776, compound

Product 1

HCID 57656882HCID 57656882, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the alkenes N-(3,4-dichlorophenyl)-4-[(1-ethylpiperidin-3-yl)methyl]-3,6-dihydropyridine-1(2H)-carboxamide and N-(3,4-dichlorophenyl)-4-[(1-ethylpiperidin-3-yl)methylene]piperidine-1-carboxamide (3:1) (40 mg) and 10% palladium on charcoal (30 mg) in ethanol (5 mL) was evacuated and purged with hydrogen. The mixture was left under an atmosphere of hydrogen for 4 hrs and then filtered through celite. The celite pad was washed with ethanol and the filtrate evaporated. The residue was purified using reverse phase HPLC eluting with a mixture of 5-95% acetonitrile in water and then by silica column chromatography, eluting with a gradient of 0 to 5% 7M NH3/MeOH in dichloromethane to give the title compound as a white solid (25 mg, 62%).

Workup

  1. customwas evacuated
  2. custompurged with hydrogen
  3. filtrationfiltered through celite
  4. washThe celite pad was washed with ethanol
  5. customthe filtrate evaporated
  6. customThe residue was purified
  7. washeluting with a mixture of 5-95% acetonitrile in water
  8. washby silica column chromatography, eluting with a gradient of 0 to 5% 7M NH3/MeOH in dichloromethane

Sources & evidence

ORD record
ord-ed25043df382460bb2d1bac4089388bf
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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