HCID 13094812, compound → HCID 57656882, compound

HRID 2371205Notes

Reaction equation

HRID 2371205 reaction equation
N1(C(N)=O)CC=CCC1.[Cl:10][C:11]1[CH:12]=[C:13]([NH:18][C:19]([N:21]2[CH2:26][CH2:25][C:24](=[CH:27][CH:28]3[CH2:33][CH2:32][CH2:31][N:30]([CH2:34][CH3:35])[CH2:29]3)[CH2:23][CH2:22]2)=[O:20])[CH:14]=[CH:15][C:16]=1[Cl:17]>[Pd].C(O)C>[Cl:10][C:11]1[CH:12]=[C:13]([NH:18][C:19]([N:21]2[CH2:22][CH2:23][CH:24]([CH2:27][CH:28]3[CH2:33][CH2:32][CH2:31][N:30]([CH2:34][CH3:35])[CH2:29]3)[CH2:25][CH2:26]2)=[O:20])[CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

5

Reactant 2

HCID 13094812HCID 13094812, compoundHCID 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-460a87e19ef84665bc5a25cf0c181bc6
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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