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

Participants

Reaction Steps

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).

Provenance & Evidence