HCID 19864507, compound → HCID 19864505, compound

HRID 1199977Notes

Reaction equation

HRID 1199977 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]3[C:18]=2[CH2:19][N:20]([CH3:27])[C:21](=[O:26])[CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:5][CH:4]=1>C(O)(=O)C.Cl.C(O)(C)C.[Rh]>[ClH:2].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH2:16][CH2:15][CH:14]([CH3:17])[CH2:13][N:12]3[C:18]=2[CH2:19][N:20]([CH3:27])[C:21](=[O:26])[CH2:22][CH:23]([CH3:24])[CH3:25])=[CH:5][CH:4]=1

Participants

6

Reactant 1

HCID 19864507HCID 19864507, compound

Product 1

HCID 19864505HCID 19864505, compoundYield 93.3%

Reagents, catalysts & solvents 4

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

3 g (8.1 mmol) of N-[{2-(4-chlorophenyl)-6-methylimidazo[1,2-a]pyridin-3-yl}methyl]-N,3-dimethylbutanamide hydrochloride is dissolved in 200 ml of acetic acid, 0.7 g of rhodium on alumina (5% rhodium) is added and the mixture is hydrogenated under a pressure of approximately 0.35 MPa (50 PSI) until absorption is complete. The catalyst is removed by filtration and the solvent evaporated off under reduced pressure. The residue is taken up with dichloromethane and the solution washed with bicarbonate water. The organic phase is separated after settling and dried over magnesium sulphate. After filtration and evaporation of the solvent, a solid residue is taken up with ether and purified by chromatography on a silica column. The hydrochloride is prepared therefrom in 0.1N hydrogen chloride in isopropyl alcohol. 1.55 g of the expected product is obtained.

Workup

  1. customthe mixture is hydrogenated under a pressure of approximately 0.35 MPa (50 PSI) until absorption
  2. customThe catalyst is removed by filtration
  3. customthe solvent evaporated off under reduced pressure
  4. washthe solution washed with bicarbonate water
  5. customThe organic phase is separated
  6. dry with materialdried over magnesium sulphate
  7. filtrationAfter filtration and evaporation of the solvent
  8. custompurified by chromatography on a silica column
  9. customThe hydrochloride is prepared

Sources & evidence

ORD record
ord-dbbe26152deb43149c322384586a64f0
Source dataset
uspto-grants-1990_02
Patent number
US04904670

Reaction notes

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