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

A solution of methylamine (8.5 mL of a 2.0 M solution in MeOH, 17 mmol) was added to 3-chloro-2-propoxybenzaldehyde (0.425 g, 2.14 mmol) and the mixture was stirred for 72 h. The solution was concentrated under reduced pressure. The resulting clear oil was dissolved in EtOH (8.5 mL) and treated with NaBH4 (0.080 g, 2.1 mmol). After stirring for 18 h, the reaction mixture was concentrated under reduced pressure and then dissolved in 1 N NaOH (10 mL). The mixture was extracted with Et2O (3×50 mL). The combined organics were washed with brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (0.441 g, 96%) as a light yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.37-7.31 (m, 2H), 7.08 (t, J=7.7 Hz, 1H), 3.85 (t, J=6.4 Hz, 2H), 3.67 (s, 2H), 2.26 (s, 3H), 2.04 (br s, 1H), 1.82-1.70 (m, 2H), 1.02 (t, J=7.3 Hz, 3H).

1. concentrationThe solution was concentrated under reduced pressure
2. dissolutionThe resulting clear oil was dissolved in EtOH (8.5 mL)
3. stirringAfter stirring for 18 h
4. concentrationthe reaction mixture was concentrated under reduced pressure
5. dissolutiondissolved in 1 N NaOH (10 mL)
6. extractionThe mixture was extracted with Et2O (3×50 mL)
7. washThe combined organics were washed with brine (2×100 mL)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated

ORD-Eintrag

ord-4c5894f5293d4c42af28ed4862d9b431

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08450307B2