Methanol → 3-(Allyloxy)-1-(3-methoxyphenyl)propan-1-amine

Participants

Reaction Steps

Step R (3): N-(3-(Allyloxy)-1-(3-methoxyphenyl)propyl)-2,2,2-trifluoroacetamide from step R (2) (610 mg, 1.92 mmol), potassium carbonate (1.33 g, 9.26 mmol), methanol (50 mL) and H2O (4 mL) were heated to reflux for 16 h. The mixture was concentrated in vacuo. H2O was added, and the aqueous layer was extracted several times with EtOAc. The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo to afford 390 mg (92% yield) of 3-(allyloxy)-1-(3-methoxyphenyl)propan-1-amine as a pale-yellow oil. The crude mixture was used without further purification. LC-MS (M+H)+=222.95; 1H NMR (300 MHz, CDCl3) δ ppm 1.82-2.18 (m, 2H) 3.23-3.54 (m, 3H) 3.72-3.82 (m, 3H) 3.83-4.00 (m, 2H) 4.14 (t, J=6.95 Hz, 1H) 5.08-5.31 (m, 2H) 5.76-5.95 (m, 1H) 6.71-6.86 (m, 1H) 6.86-6.97 (m, 1H) 7.14-7.29 (m, 2H).

Provenance & Evidence