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Chlorproethazine

Chlorproethazine

Chlorproethazine, sold under the brand name Neuriplege, is a drug of the phenothiazine group described as a muscle relaxant or tranquilizer which is or has been marketed in Europe as a topical cream for the treatment of muscle pain. It has been associated with photoallergic contact dermatitis.

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.

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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 Ullmann condensation (i.e. the Goldberg reaction).

References

References

  1. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
  2. (2000). "Index Nominum 2000: International Drug Directory". Taylor & Francis.
  3. (6 December 2012). "Concise Dictionary of Pharmacological Agents: Properties and Synonyms". Springer Science & Business Media.
  4. William Andrew Publishing. (22 October 2013). "Pharmaceutical Manufacturing Encyclopedia". Elsevier.
  5. "Chlorproethazine". Drugs.com.
  6. (2008). "Fisher's Contact Dermatitis". PMPH-USA.
  7. (29 September 2010). "Contact Dermatitis". Springer Science & Business Media.
  8. "Preparation of Phenothiazine Compounds".
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analgesics chloroarenes phenothiazines diethylamino-compounds
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