Methylamine → 2-[Methyl-(2-methyl-benzyl)-amino]-1-naphthalen-2-yl-ethanol

Participants

Reaction Steps

o-Tolualdehyde was converted to methyl-(2-methyl-benzyl)-amine via reductive amination using aqueous methyl amine and NaBH4. Methyl-(2-methyl-benzyl)-amine was then alkylated with 2-bromo-2′-acetonaphthone followed by reduction by NaBH4 to give 2-[methyl-(2-methyl-benzyl)-amino]-1-naphthalen-2-yl-ethanol as a clear, light yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.78-7.87 (m, 4 H), 7.40-7.51 (m, 3 H), 7.14-7.30 (m, 4 H), 4.89 (dd, J=10.1, 3.9 Hz, 1 H), 3.71 (d, J=12.9 Hz, 1 H), 3.54 (d, J=12.9 Hz, 1 H), 2.70 (dd, J=12.3, 10.3 Hz, 1 H), 2.62 (dd, J=12.4, 3.9 Hz, 1 H), 2.41 (s, 3 H), 2.35 (s, 3 H); Cl MS m/z 306 [C21H23NO+H]+.

Provenance & Evidence