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,

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 기록

ord-2b7d6640b1cb4fe69ad2e839e9b50887

출처 데이터셋

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08450307B2