Nitrogen → 1-(4-Methoxyphenyl)propan-1-amine

HRID 2301937Notes

Reaction equation

HRID 2301937 reaction equation
N#N.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:14]O)[CH2:12][CH3:13])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.O.[Pd]>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH2:14])[CH2:12][CH3:13])=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 534338901-(4-Methoxyphenyl)propan-1-one oxime

Product 1

HCID 31432871-(4-Methoxyphenyl)propan-1-amineYield 83%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a N2 flushed solution of 4′-methoxypropiophenone oxime (4 grams, 22.3 mmol) in glacial acetic acid (40 milliliters) was added 0.8 grams of 5% Pd/C. The mixture was treated with 60 psi of H2 in a Parr Type Shaker for 23 hours. The catalyst was filtered off through celite and the filtrate was concentrated to afford a yellow oil. The oil was taken up in water, the pH was adjusted to 12 using a saturated solution of sodium carbonate, and extracted with methylene chloride. The organic extract was dried over magnesium sulfate and concentrated to afford 3.04 grams (83%) of product as a yellow oil: 1H NMR (CDCl3) δ7.32-7.20(m, 2H), 6.94-6.82(m, 2H), 3.79(s, 3H), 1.88-1.54(m, 4H), 0.87(t, J=7.4 Hz, 3H).

Workup

  1. additionThe mixture was treated with 60 psi of H2 in a Parr Type Shaker for 23 hours
  2. filtrationThe catalyst was filtered off through celite
  3. concentrationthe filtrate was concentrated
  4. customto afford a yellow oil
  5. extractionextracted with methylene chloride
  6. extractionThe organic extract
  7. dry with materialwas dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2fbcdb9d748b4e5ebc57b45b4594479c
Source dataset
uspto-grants-2002_08
Patent number
US06429221B1

Reaction notes

Loading…