184906-26-1 → HCID 10655861, compound

HRID 1737303Notes

Reaction equation

HRID 1737303 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][C:10]2[C:5](=[CH:6][C:7]([CH3:14])=[C:8]([OH:13])[C:9]=2[CH3:12])[CH:4]=[N:3]1>CCO.[Ni]>[CH3:1][C:2]1([CH3:15])[CH2:11][C:10]2[C:5](=[CH:6][C:7]([CH3:14])=[C:8]([OH:13])[C:9]=2[CH3:12])[CH2:4][NH:3]1

Participants

4

Reactant 1

HCID 135480532184906-26-1

Product 1

HCID 10655861HCID 10655861, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Imine 38 (1.00 g, 4.93 mmol) is hydrogenated (50 psi H2) over RaNi (spatula scoop, washed 3×with water and 3×with EtOH) in EtOH (20 mL) for 2 h at rt. Filtration of the reaction mixture through filter aid and evaporation of the solvent gives the amine as a light yellow solid (MW=205.3) which is used without further purification. Yield: 0.90 g (89%) . 1H NMR (CDCl3) 6.68 (s, 1), 3.95 (s, 2), 3.62 (br s, 2), 2.45 (s, 2), 2.21 (s, 3), 2.08 (s, 3), 1.20 (s, 6); 13C NMR (CDCl3) 150.43, 131.39, 125.87, 125.12, 122.19, 121.16, 48.85, 43.93, 38.98, 27.89, 16.01, 10.97.

Workup

  1. customfor 2 h
  2. customat rt
  3. filtrationFiltration of the reaction mixture
  4. filtrationthrough filter
  5. customaid and evaporation of the solvent

Sources & evidence

ORD record
ord-2b81e03cdd4f4d238a09da4134858117
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

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