4-(3-Methoxyphenyl)butanenitrile → Benzenebutanamine, 3-methoxy-

HRID 1736504Notes

Reaction equation

HRID 1736504 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][C:12]#[N:13])[CH:6]=[CH:7][CH:8]=1.[H][H]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 5789544-(3-Methoxyphenyl)butanenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 542611Benzenebutanamine, 3-methoxy-Yield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a Parr bottle flushed with nitrogen was added ~1.0 g of Raney Nickel (50% suspension in H2O), ethanol (125 mL), ammonium hydroxide (30 mL), and a solution of 4-(3-methoxyphenyl)butyronitrile (8.49 g, 48.4 mmol) in ethanol (150 mL). The bottle was charged with hydrogen (60 psi) and rocked 3 d. The suspension was filtered through Celite, the cake rinsed with fresh ethanol (400 mL), and the combined filtrate concentrated in vacuo. The resulting suspension was treated with dichloromethane (200 mL) and water (200 mL), the layers separated, and the aqueous portion back-extracted with fresh dichloromethane (2×50 mL). The combined organic portions were washed with saturated sodium chloride solution (300 mL), dried (K2CO3), filtered, and concentrated in vacuo. Kugelrohr distillation (0.1 torr, 120° C.) provided the desired product as a clear liquid (6.77 g, 78%) which was identical spectroscopically to that previously reported. Venit, J. J.; DiPierro, M.; Magnus, P. J. Org. Chem. 1989, 54, 4298-4301. 1H NMR (CDCl3) δ 7.20 (t, J=8 Hz, 1H), 6.79-6.70 (m, 3H), 3.80 (s, 3H), 2.75-2.68 (m, 2H), 2.61 t J=8 Hz, 2H), 1.82-1.45 (m, 6H).

Workup

  1. customTo a Parr bottle flushed with nitrogen
  2. additionwas added ~1.0 g of Raney Nickel (50% suspension in H2O), ethanol (125 mL), ammonium hydroxide (30 mL)
  3. filtrationThe suspension was filtered through Celite
  4. washthe cake rinsed with fresh ethanol (400 mL)
  5. concentrationthe combined filtrate concentrated in vacuo
  6. additionThe resulting suspension was treated with dichloromethane (200 mL) and water (200 mL)
  7. customthe layers separated
  8. extractionthe aqueous portion back-extracted with fresh dichloromethane (2×50 mL)
  9. washThe combined organic portions were washed with saturated sodium chloride solution (300 mL)
  10. dry with materialdried (K2CO3)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. distillationKugelrohr distillation (0.1 torr, 120° C.)

Sources & evidence

ORD record
ord-ae8bf134731b45fe977a2f0cf60ea28e
Source dataset
uspto-grants-1996_07
Patent number
US05541228

Reaction notes

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