DAPAWMLLUHGJNN-UHFFFAOYSA-N synthesis

Yield:1172995-13-9 96%

Reaction Conditions:

Stage #1: stearic acid;paliperidonewith dmap;benzoyl chloride;triethylamine in tetrahydrofuran at 20; for 24 h;
Stage #2: with water in tetrahydrofuran at 20; for 1 h;

Steps:

19

A 100 ml flask equipped with a magnetic stirrer is charged with paliperidone (5 g, 11.7 mmol, 1 eq), stearic acid (3.33 g, 11.7 mmol, 1 eq), 4-dimethylaminopyridine (0.36 g, 2.95 mmol, 0.25 eq), triethylamine (3.25 ml, 23.3 mmol, 2 eq) and tetrahydrofuran (50 ml). The suspension is stirred at room temperature for 15 minutes. Benzoyl chloride (1.55 ml, 13.34 mmol, 1.1 eq) is added drop-wise and the suspension is further stirred at room temperature for 24 hours. Water (50 ml) is then added and the suspension is further stirred for 1 hour then filtered off under vacuum, washed with water and dried at 50°C under vacuum. The resulting solid is paliperidone stearate. Yield: 96% by wt.

References:

WO2009/89076,2009,A2 Location in patent:Page/Page column 30