(R)-3-Methylmorpholine hydrochloride Chemical Properties

Melting point:

123.0 to 127.0 °C

storage temp. 

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

form 

powder to crystal

color 

White to Orange to Green

Safety Information

HS Code 

2934999090

(R)-3-Methylmorpholine hydrochloride Usage And Synthesis

Uses

(3R)-3-Methylmorpholine Hydrochloride is used in the discovery studies of novel 2-(alkylmorpholin-4-yl)-6-(3-fluoropyridin-4-yl)-pyrimidin-4(3H)-ones as orally active GSK-3β inhibitors for Alzheimer''s disease

Synthesis

General procedure for the synthesis of (R)-3-methylmorpholine hydrochloride from the compound (CAS: 954133-47-2): to a solution of (5R)-4-(4-methoxybenzyl)-5-methylmorpholine (17.8 g, 80.3 mmol) in 1,2-dichloroethane (180 mL) was added 1-chloroethyl chloroformate (46 g, 322 mmol). The reaction mixture was stirred at 80 °C for 6 hours. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure. The residue was dissolved in methanol (180 mL) and stirred at 80 °C for 1 hour. The solvent was again removed by evaporation under reduced pressure and the residue was washed with ethyl acetate and dried to give (3R)-3-methylmorpholine hydrochloride (8.2 g, 59.6 mmol, 74% yield) as white crystals.

References

[1] Patent: WO2007/119463, 2007, A1. Location in patent: Page/Page column 197; 198
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 5, p. 1086 - 1091

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