Racemic Resolution of Praziquantel and Praziquanamine

 

Mnr: 11-20


Hazard and Risk Assessment:
Procedure
To a cooled solution of MNR7-6 (7.1 g, 35.11 mmol) in DCM (170 mL) at 0°C was added triethylamine (7.34 mL, 52.66 mmol) and benzoyl chloride (4.48 mL, 38.62 mmol). The solution was stirred for 14 hours at room temperature.
In the morning, the reaction was quenched with water (mL) and stirred for 30 minutes then the organic layer was separated and washed with sodium carbonate solution (mL), 1M HCl (ml) and brine (mL), dried and filtered to give the crude as a white solid, the crude was then purified by FCC (50-100% EtOAc/Hex)

fracs 15-39 9.34 g, 30.5 mmol, 87% Yield

NMR

1H NMR (500 MHz, CDCl3) δ 7.35-7.41 (5H, m), 7.29-7.15 (4H, m), 5,25 (1H, br), 4.99 (1H, br), 4.81 (1H, br), 4.36 (1H, br), 4.09 (1H, br), 3.07 (1H, br), 3.03-2.93 (1H, m), 2.93-2.84 (1H, m), 2.83-2.73 (1H, m).

IR (film) 1704, 1633, 1066 cm-1

Lit M.p. 158-160°C Kiec'-Kononowicz, K. Archiv der Pharmazie 1989, 322, 795