Methylamine → (3-Chloro-2-isopropoxybenzyl)methylamine

Methylamine (10.3 mL of a 2.0 M solution in MeOH, 20.6 mmol) was added to 3-chloro-2-isopropoxybenzaldehyde (0.500 g, 2.52 mmol) and the mixture was stirred for 72 h. The solution was concentrated under reduced pressure. The resulting light yellow oil was dissolved in EtOH (10.3 mL) and treated with NaBH4 (0.095 g, 2.52 mmol). After stirring for 18 h, the reaction mixture was concentrated under reduced pressure, dissolved in 1 N NaOH (20 mL) and extracted with Et2O (3×50 mL). The combined organics were washed with brine (2×75 mL), dried (Na2SO4) and concentrated to give the title compound (0.50 g, 93%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.40-7.31 (m, 2H), 7.08 (t, J=7.8 Hz, 1H), 4.42 (q, J=6.1 Hz, 1H), 3.66 (s, 2H), 2.25 (s, 3H), 2.02 (br s, 1H), 1.25 (d, J=6.1 Hz, 6H).

1. concentrationThe solution was concentrated under reduced pressure
2. dissolutionThe resulting light yellow oil was dissolved in EtOH (10.3 mL)
3. stirringAfter stirring for 18 h
4. concentrationthe reaction mixture was concentrated under reduced pressure
5. dissolutiondissolved in 1 N NaOH (20 mL)
6. extractionextracted with Et2O (3×50 mL)
7. washThe combined organics were washed with brine (2×75 mL)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated

ORD-Eintrag

ord-f9ee577666b54ade86bf7b28ecbd10b9

Quelldatensatz

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07879872B2