- Synthesis of Setoperone
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Setoperone (CAS NO.: ), with its systematic name of 5H-Thiazolo(3,2-a)pyrimidin-5-one, 6-(2-(4-(4-fluorobenzoyl)-1-piperidinyl)ethyl)-2,3-dihydro-7-methyl-, could be produced through many synthetic methods.
Following is one of the reaction routes:
4-(4-Fluorobenzoyl)piperidine (IX) is condensed with 6-(2-bromo ethyl)-7-methyl-2,3-dihydro-5H-thiazolo[2,3-a]pyrimidin-5-one (IV) in the presence of Na2CO3 in refluxing 4-methyl-2-pentanone to produce the final product Setoperone.
And the starting products are obtained as follows: 4-Hydroxy-5-(2-hydroxyethyl)-6-methyl-2-mercaptopyrimidine (I) is cyclized with 1,2-dibromo ethane (II) to produce 2,3-dihydro-6-(2-hydroxyethyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one (II) in the presence of K2CO3 in hot dimethylacetamide, which by reaction with HBr in refluxing acetic acid is converted to the corresponding 6-(2-bromoethyl) derivative (IV).The Grignard reaction of 4-bromo (V) with N benzyl-4 cyanopiperidine (VI) by means of Mg in dimethoxyethane gives 4-(4-fluorobenzoyl)-N-benzylpiperidine (VII), which is treated with ethyl chlorocarbo-nate in refluxing toluene to afford ethyl 4-(4-fluorobenzoyl)piperidine-1-carboxylate (VIII). At last, this compound is treated with HBr in refluxing 48% HBr to afford (IX).
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