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

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).

1. concentrationThe solution was concentrated under reduced pressure
2. dissolutionThe resulting dark yellow oil was dissolved in EtOH (30 mL)
3. waitAfter 18 h
4. concentrationthe reaction mixture was concentrated under reduced pressure
5. dissolutiondissolved in 1 N NaOH (30 mL)
6. extractionThe mixture was extracted with Et2O (3×75 mL)
7. dry with materialThe combined organics were dried (Na2SO4)
8. concentrationconcentrated

ORD record

ord-faf887179cc74b1c9b4c01ff6371219d

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2