HCID 21710454, compound → HCID 21710466, compound

HRID 650943Notes

Reaction equation

HRID 650943 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6](CC1C=CC=CC=1)[CH:7]2[CH3:12]>C(O)C.[Pd]>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH:7]2[CH3:12]

Participants

4

Reactant 1

HCID 21710454HCID 21710454, compound

Product 1

HCID 21710466HCID 21710466, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Amino-2-benzyl-1-methyl-1,2-dihydroisoquinoline (4.5 g, 17.9 mmol) was dissolved in ethanol (250 ml); 10% palladium catalyst on activated carbon (1 g) was then added and the mixture hydrogenated at atmospheric pressure for 24 h. The catalyst was then removed by filtration through Kieselguhr and the solvent removed in vacuo to afford a brown solid. This residue was then subjected to column chromatography eluting with 5 to 10% methanol-dichloromethane. The relevant fractions were combined and concentrated in vacuo to afford a brown solid (1.26 g).

Workup

  1. customThe catalyst was then removed by filtration through Kieselguhr
  2. customthe solvent removed in vacuo
  3. customto afford a brown solid
  4. washeluting with 5 to 10% methanol-dichloromethane
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-455ab767c05e4131969d31818be8c7ab
Source dataset
uspto-grants-2001_08
Patent number
US06277861B1

Reaction notes

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