Chlorproethazine

Chlorproethazine

Names
IUPAC name 3-(2-chlorophenothiazin-10-yl)-N,N-diethylpropan-1-amine
Identifiers
CAS Number	84-01-5 Y 4611-02-3 N
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL2105938 N
ChemSpider	59173 N
ECHA InfoCard	100.001.373
KEGG	D07308 Y
PubChem	65750 65750
UNII	960NX27Z07 Y
InChI InChI=1S/C19H23ClN2S/c1-3-21(4-2)12-7-13-22-16-8-5-6-9-18(16)23-19-11-10-15(20)14-17(19)22/h5-6,8-11,14H,3-4,7,12-13H2,1-2H3 N Key: DBOUGBAQLIXZLV-UHFFFAOYSA-N N InChI=1/C19H23ClN2S/c1-3-21(4-2)12-7-13-22-16-8-5-6-9-18(16)23-19-11-10-15(20)14-17(19)22/h5-6,8-11,14H,3-4,7,12-13H2,1-2H3 Key: DBOUGBAQLIXZLV-UHFFFAOYAP
SMILES Clc2cc1N(c3c(Sc1cc2)cccc3)CCCN(CC)CC
Properties
Chemical formula	C19H23ClN2S
Molar mass	346.91732 g/mol
Pharmacology
ATC code	N05AA07 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chlorproethazine is an antipsychotic.

Synthesis

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.

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.