Ammonia → HCID 13342875, compound

Participants

Reaction Steps

A solution of N,N-dipropyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine (17.6 g, 0.067 mole) in tetrahydrofuran (188 mL) and isopropanol (188 mL) was added with stirring to liquid ammonia (500 mL) cooled by a dry ice-isopropanol bath. Sodium (29.4 g, 1.3 g-atom) was added in small pieces over 0.5 hr. After the blue colour disappeared (ca. 2 hr), methanol (120 mL) was added and the ammonia was allowed to evaporate after removal of the cooling bath. The residue was diluted with water (1000 mL) and extracted three times with diethyl ether. The ether extracts were dried (MgSO4) and concentrated, giving a yellow oil (15.8 g) of 1,2,3,4,5,8-hexahydro-6-methoxy-N,N-dipropyl-2-naphthalenamine, NMR (CDCl3) δ 0.85 (t, 6H), 3.5 (s, 3H) and 4.6 (m, 1H).

Provenance & Evidence