Methylamine → Methyl-(1-propyl-naphthalen-2-ylmethyl)amine

Participants

Reaction Steps

A solution of 2.0 M methylamine in methanol (20 mL) was added to 1-propyl-naphthalene-2-carbaldehyde (0.983 g, 4.95 mmol) under N2 and allowed to stir for 18 h. The solution was concentrated under reduced pressure. Then the resulting dark yellow oil was solvated in EtOH (20 mL) under N2. To the solution was added NaBH4 (0.187 g, 4.95 mmol) and the mixture allowed to stir for 6.5 h. The reaction was concentrated under reduced pressure, then solvated in 1 N NaOH (20 mL) and extracted with Et2O (3×50 mL). The organics were combined, washed with brine (2×100 mL), dried over Na2SO4, filtered and concentrated to yield the title compound (0.94 g, 89%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.87-7.73 (m, 4H), 7.51-7.43 (m, 3H), 3.53 (m, 1H), 2.09 (s, 3H), 1.70-1.52 (m, 2H), 1.26-1.12 (m, 2H), 0.87-0.79 (m, 3H).

Provenance & Evidence