Hydrochloric Acid → HCID 15171524, compound

HRID 728199Notes

Reaction equation

HRID 728199 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]3[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]3[CH:19]=2)=[CH:4][CH:3]=1.Cl>[Pd].CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]3[CH2:17][CH:16]([CH3:18])[CH2:15][CH2:14][N:13]3[CH:19]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10083527HCID 10083527, compound

Product 1

HCID 15171524HCID 15171524, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (1.0 g) was added to a mixture of 2-[2-(4-aminophenyl)ethyl]-7-methylimidazo[1,2-a]pyridine (4.0 g) in methanol (100 ml) and 1N-hydrochloric acid (60 ml) and the mixture was subjected to catalytic reduction at ambient temperature under atmospheric pressure. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. To the residue was added a mixture of ethyl acetate and water and the mixture was adjusted to pH 8 with potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated and the residue was triturated with a solution of diethyl ether and ethyl acetate. The precipitate was collected by filtration and dried to give 2-[2-(4-aminophenyl)ethyl]-7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (3.39 g).

Workup

  1. customwas subjected to catalytic reduction at ambient temperature under atmospheric pressure
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. additionTo the residue was added
  5. additiona mixture of ethyl acetate and water
  6. washThe separated organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was triturated with a solution of diethyl ether and ethyl acetate
  10. filtrationThe precipitate was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-63335267b9494b859e883f9a2818abda
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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