Chlorproethazine

Source: Wikipedia, the free encyclopedia.
Chlorproethazine
Names
Preferred IUPAC name
3-(2-Chlorophenothiazin-10-yl)-N,N-diethylpropan-1-amine
Other names
RP-4909
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.001.373 Edit this at Wikidata
KEGG
UNII
  • 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
C19H23ClN2S
Molar mass 346.91732 g/mol
Pharmacology
N05AA07 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Chlorproethazine, sold under the brand name Neuriplege, is a

photoallergic contact dermatitis.[6][7]

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.

Patent:[8]

Thus alkylation of 2-(2-bromo-phenylsulfanyl)-5-chloro-aniline [105790-02-1] (1) with 3-chloro-1-diethylaminopropane [104-77-8] (2) leads to the intermediate (3). Ring closure as above by nucleophilic aromatic displacement leads to the antipsychotic drug chlorproethazine (4).

The last step uses copper powder and is a form of the

Goldberg reaction
).

References

  1. ISBN 978-1-4757-2085-3
    .
  2. ISBN 978-3-88763-075-1
    .
  3. ISBN 978-94-011-4439-1
    .
  4. ISBN 978-0-8155-1856-3
    .
  5. ^ "Chlorproethazine". Drugs.com. Archived from the original on 27 September 2017.
  6. ISBN 978-1-55009-378-0
    .
  7. ISBN 978-3-642-03827-3
    .
  8. ^ US 2769002, Buisson P, Gailliot P, "Preparation of Phenothiazine Compounds", issued 30 October 1956, assigned to Rhône-Poulenc 


Retrieved from "https://en.wikipedia.org/w/index.php?title=Chlorproethazine&oldid=1262080663"