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ChemicalBook CAS DataBase List Paliperidone
144598-75-4

Paliperidone synthesis

11synthesis methods
The synthesis of paliperidone involves the reaction of 2-acetyl-g-butyrolactone with 2-amino-3-benzyloxypyridine in the presence of phosphoryl chloride. The benzyl protecting group of the intermediate 9-benzyloxy- 3-(2-chloroethyl)-2-methylpyrido[1,2-a]pyrimidin-4-one is then removed by hydrogenolysis over Pd/C followed by the nucleophilic displacement of the chlorine with 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole to provide racemic paliperidone. While paliperidone can be resolved, both enantiomers are equipotent and interconvert in vivo obviating the need for separation.
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Yield:144598-75-4 100%

Reaction Conditions:

with ammonium hydroxide in water;

Steps:

3

. Paliperidone was obtained in quantitative yield from the oxalate salt (7.2 g, 13.9 mmol) by treatment with 20% ammonium hydroxide and extraction in dichloromethane (50 mL), washing with brine, drying the organic extract over sodium sulphate and concentrating to a solid residue. Paliperidone was optionally recrystallized from acetonitrile.

References:

EP2199293,2010,A1 Location in patent:Page/Page column 6

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