2-METHOXY-N-METHYLBENZYLAMINE 97 Chemical Properties

Boiling point:

234-235 °C(lit.)

Density 

1.015 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.5325(lit.)

Flash point:

222 °F

storage temp. 

2-8°C(protect from light)

form 

Liquid

color 

Colorless

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

8

HS Code 

2922290090

2-METHOXY-N-METHYLBENZYLAMINE 97 Usage And Synthesis

Synthesis

Step A: 2-methoxybenzaldehyde (5.56 g, 40 mmol) was dissolved in methanol (40 mL) and methylamine (40 wt% aqueous solution, 6.9 mL, 80 mmol) and acetic acid (240 mg, 4 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 16 h and then cooled in an ice bath. Sodium borohydride (1.51 g, 40 mmol) was added in batches under ice bath cooling conditions. After addition, the reaction mixture was continued to stir at room temperature for 3 hours. After completion of the reaction, most of the solvent was removed by concentration under reduced pressure. The residue was diluted with distilled water (100 mL) and ethyl acetate (100 mL) and partitioned. The aqueous phase was extracted with ethyl acetate (2 × 100 mL) and the organic phases were combined. The organic phase was washed sequentially with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford the target product N-methyl-2-methoxybenzylamine (4.7 g, 79% yield). The product was characterized by 1H NMR (CDCl3, 500 MHz): δ 7.23 (d, J = 7.4 Hz, 2H), 6.91 (t, J = 7.4 Hz, 1H), 6.86 (d, J = 7.9 Hz, 1H), 3.83 (s, 3H), 3.75 (s, 2H), 2.42 (s, 3H); ESI MS m/z = 152 [M + H]+. The crude product obtained can be used directly in the subsequent reaction without further purification.

References

[1] Patent: US2006/52378, 2006, A1. Location in patent: Page/Page column 144
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2539 - 2543
[3] Journal of the American Chemical Society, 1944, vol. 66, p. 1875,1879
[4] European Journal of Medicinal Chemistry, 2014, vol. 76, p. 314 - 331
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 911 - 923

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