METHYLPYRIDIN-2-YLMETHYLAMINE DIHYDROCHLORIDE Chemical Properties

Melting point:

64 °C

Boiling point:

78-80 °C(Press: 10 Torr)

Density 

0.994 g/mL at 25 °C

refractive index 

n20/D1.524

Flash point:

82℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

pK1:2.92(＋2);pK2:8.82(＋1) (30°C)

form 

liquid

color 

Colorless

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-37/38-41

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

METHYLPYRIDIN-2-YLMETHYLAMINE DIHYDROCHLORIDE Usage And Synthesis

Uses

2-[(Methylamino)methyl]pyridine is used as a reagent in the preparation and structure activity relationship of imidazolopyrimidones as gonadotropin-releasing hormone (GnRH) receptor antagonists.

Synthesis

The general procedure for the synthesis of N-methyl-1-pyridine-2-methylamine from pyridine-2-carbaldehyde is as follows: 1. Preparation of 2-(methylaminomethyl)pyridine: 10.7 g (100 mmol) of pyridine-2-carbaldehyde was dissolved in 60 ml of benzene, and methylamine gas was passed through and bubbled for 2 hours. After completion of the reaction, the benzene was removed by distillation under reduced pressure. The residue was dissolved in 40 ml of ethanol. 2. Reduction reaction: Add 5.7g NaBH4 to the above ethanol solution in batches and stir the reaction mixture for 8 hours at room temperature. 3. Post-treatment: 0.5N hydrochloric acid was slowly added to the reaction mixture and the pH was adjusted to not less than 6. Subsequently, 300 ml of dichloromethane was added, and the organic layer was washed three times with 1M NaHCO3 solution at pH 10. 4. Purification of product: The organic layers were combined and concentrated under reduced pressure to give 10.4 g of N-methyl-1-pyridine-2-methylamine in 85% yield. Product characterization: 1H NMR (CDCl3) δ 2.1 (s, 1H), 2.5 (s, 3H), 3.9 (s, 2H), 7.1 (t, 1H), 7.3 (d, 1H), 7.6 (t, 1H), 8.5 (d, 1H).

References

[1] Patent: US5587388, 1996, A
[2] Patent: EP601486, 1994, A1
[3] Magnetic Resonance in Chemistry, 1987, vol. 25, p. 696 - 706

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