Chlorproethazine

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Chlorproethazine
Chlorproethazine.png
Names
IUPAC name
3-(2-chlorophenothiazin-10-yl)-N,N-diethylpropan-1-amine
Identifiers
ATC code N05AA07
84-01-5 YesY
4611-02-3 N
ChEMBL ChEMBL2105938 N
ChemSpider 59173 N
Jmol-3D images Image
KEGG D07308 YesY
PubChem 65750
65750
Properties
C19H23ClN2S
Molar mass 346.91732 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Chlorproethazine is an antipsychotic.

Synthesis[edit]

Chlorproethazine can be synthesized from a diphenylsulfide derivative. The general scheme is sufficiently flexible to permit the interchange of the order of some of the steps.

Chlorproethazine syn.png

Thus alkylation of aniline thioether () with 3-chloro-1-diethylaminopropane leads to the intermediate (). Ring closure as above by nucleophilic aromatic displacement leads to the antipsychotic drug chlorproethazine.[1]

References[edit]

  1. ^ Buisson, P.; Gailliot, P.; 1956, U.S. Patent 2,769,002