Methylamine → (2-Ethoxy-3-isopropylbenzyl)methylamine

A solution of methylamine (30 mL of a 2.0 M solution, 60 mmol) was added to 2-ethoxy-3-isopropylbenzaldehyde (1.49 g, 7.75 mmol) and the mixture was stirred for 72 h. The solution was concentrated under reduced pressure. The residue was dissolved in EtOH (30 mL) and treated with NaBH4 (0.293 g, 7.75 mmol). After stirring for 18 h, the reaction mixture was concentrated under reduced pressure and then dissolved in 1 N NaOH (30 mL). The mixture was extracted with Et2O (3×50 mL). The combined organics were collected, washed with brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (1.51 g, 94%) as a light yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.21-7.13 (m, 2H), 7.04 (t, J=7.5 Hz, 1H), 3.79 (q, J=7.0 Hz, 2H), 3.63 (s, 2H), 3.28-3.23 (m, 1H), 2.29 (s, 3H), 1.93 (br s, 1H), 1.35 (t, J=3.8 Hz, 3H), 1.16 (d, J=6.9 Hz, 6H).

1. concentrationThe solution was concentrated under reduced pressure
2. dissolutionThe residue was dissolved in EtOH (30 mL)
3. stirringAfter stirring for 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 (3×50 mL)
7. customThe combined organics were collected
8. washwashed with brine (2×100 mL)
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated

ORD record

ord-400c00791d104ac8aae35175542b39ae

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2