Phenaglycodol

Last updated

Phenaglycodol
Phenaglycodol.svg
Clinical data
ATC code
  • None
Legal status
Legal status
Identifiers
  • 2-(4-chlorophenyl)-3-methyl-2,3-butanediol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.124 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H15ClO2
Molar mass 214.69 g·mol−1
3D model (JSmol)
  • CC(C)(C(C)(c1ccc(cc1)Cl)O)O
  • InChI=1S/C11H15ClO2/c1-10(2,13)11(3,14)8-4-6-9(12)7-5-8/h4-7,13-14H,1-3H3
  • Key:HTYIXCKSEQQCJO-UHFFFAOYSA-N

Phenaglycodol (brand names Acalmid, Acalo, Alterton, Atadiol, Felixyn, Neotran, Pausital, Remin, Sedapsin, Sinforil, Stesil, Ultran) [2] is a drug described as a tranquilizer or sedative which has anxiolytic and anticonvulsant properties. [3] [4] It is related pharmacologically to meprobamate, though it is not a carbamate. [5] [6]

Contents

Synthesis

p-Chloroacetophenone and potassium cyanide (KCN) are reacted together via a Strecker reaction to give the corresponding cyanohydrin (3). The cyano group is then hydrated in acid to the corresponding amide, p-chloroatrolactamide (4). The amide group is then further hydrolyzed with a second equivalent of water in concentrated lye to give p-chloroatrolactic acid (5). Esterification then provides ethyl p-chloroatrolactate (6). Finally, nucleophilic addition with methylmagnesium iodide give phenaglycodol (7) crystals. [7] [8]

Phenaglycodol synthesis.svg

In a second method, a mixed pinacol coupling reaction between 4-chloroacetophenoneand acetone with magnesium activated with a small amount of trimethylsilyl chloride gave a 40% yield of phenglycodol. [9]

One-step method Phenaglycodol synthesis2.svg
One-step method

See also

Related Research Articles

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References

  1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. Usdin E, Efron DH, U.S. National Institute of Mental Health (1972). Psychotropic drugs and related compounds. National Institute of Mental Health; [for sale by the Supt. of Docs., U.S. Govt. Print. Off., Washington. ISBN   9780080255101.
  3. Vida J (19 July 2013). Anticonvulsants. Elsevier. pp. 578–. ISBN   978-0-323-14395-0.
  4. Haddad LM, Winchester JF (1983). Clinical Management of Poisoning and Drug Overdose . Saunders. ISBN   978-0-7216-4447-9.
  5. Drill VA (1958). Pharmacology in Medicine: A Collaborative Textbook. McGraw-Hill.
  6. Beckman H (1961). Pharmacology; the nature, action and use of drugs. Saunders.
  7. US 2812363,Mills J,"2-Chlorophenyl-3-methyl-2,3-butanediols",issued 5 November 1957, assigned to Eli Lilly Co.
  8. GB 788896,Mills J,"Improvements in or relating to novel substituted butanediol",published 1958-01-08, assigned to Eli Lilly & Co.
  9. Maekawa H, Yamamoto Y, Shimada H, Yonemura K, Nishiguchi I (2004). "Mg-promoted mixed pinacol coupling". Tetrahedron Letters. 45 (20): 3869–3872. doi:10.1016/j.tetlet.2004.03.109.

Further reading