Methylamine → (3-Isopropyl-2-propoxybenzyl)methylamine

Reaction equation

[CH3:1][NH2:2].[CH:3]([C:6]1[C:7]([O:14][CH2:15][CH2:16][CH3:17])=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O)([CH3:5])[CH3:4].[BH4-].[Na+]>CO>[CH:3]([C:6]1[C:7]([O:14][CH2:15][CH2:16][CH3:17])=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][CH2:1][NH2:2])([CH3:5])[CH3:4]

Participants

Procedure

A solution of methylamine (30 mL of a 2.0 M solution in MeOH, 60 mmol) was added to 3-isopropyl-2-propoxybenzaldehyde (1.49 g, 7.22 mmol) and the mixture was stirred for 72 h. The solution was concentrated under reduced pressure. The resulting dark yellow oil was dissolved in EtOH (30 mL) and treated with NaBH4 (0.273 g, 7.22 mmol). After 18 h, the reaction mixture was concentrated under reduced pressure and dissolved in 1 N NaOH (30 mL). The mixture was extracted with Et2O (3×75 mL). The combined organics were dried (Na2SO4) and concentrated to yield the title compound (1.52 g, 95%) as an orange oil: 1H NMR (300 MHz, DMSO-d6) δ 7.21-7.14 (m, 2H), 7.04 (t, J=7.5 Hz, 1H), 3.70 (t, J=6.3 Hz, 2H), 3.63 (s, 2H), 3.32-3.23 (m, 1H), 2.28 (s, 3H), 1.78 (br s, 1H), 1.76-1.71 (m, 2H), 1.16 (d, J=6.9 Hz, 6H), 1.03 (t, J=7.3 Hz, 3H).