Lorpiprazole

Lorpiprazole (INN) (brand name Normarex) is a marketed anxiolytic drug of the phenylpiperazine group.[1][2][3] It has been described as a serotonin antagonist and reuptake inhibitor (SARI) in the same group as trazodone, nefazodone, and etoperidone.[3]

Lorpiprazole
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
IUPAC name
  • (5aR,8aS)-3-(2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl)-5,5a,6,7,8,8a-hexahydrocyclopenta[3,4]pyrrolo[2,1-c][1,2,4]triazole
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H26F3N5
Molar mass405.469 g·mol−1
3D model (JSmol)
SMILES
  • FC(F)(F)c1cc(ccc1)N5CCN(CCc4nnc2n4C[C@@H]3CCC[C@H]23)CC5

Synthesis
Patent (Ex 4):[4]

The alkylation between TFMPP (1) and ethyl bromoacetate [105-36-2] (2) gives ethyl 2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]acetate, CID:22199202 (3). Hydrazinolysis of the ester with hydrazine leads to 2-[4-[3-(Trifluoromethyl)phenyl]piperazin-1-yl]acetohydrazide, CID:63572278 (4).

The reaction of 2-oxo-3-azabicyclo(3,3,0)octane [56593-76-1] (5) with Dimethylsulfate [77-78-1] (6) gives the enol ether and hence 2-methoxy-3-azabicyclo(3,3,-0)oct-2-ene, CID:13748840 (7).

Convergent synthesis completed the synthesis of Lorpiprazole (8).

See also

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 742–. ISBN 978-1-4757-2085-3.
  2. Negwer M, Scharnow H (2001). Organic-Chemical Drugs and Their Synonyms. Vol. 1–6 (8th ed.). Weinheim: Wiley-VCH. ISBN 3-527-30247-6.
  3. Fagiolini A, Comandini A, Catena Dell'Osso M, Kasper S (December 2012). "Rediscovering trazodone for the treatment of major depressive disorder". CNS Drugs. 26 (12): 1033–49. doi:10.1007/s40263-012-0010-5. PMC 3693429. PMID 23192413.
  4. Michel Wierzbicki, et al. EP 0199641 (1988 to Adir Et Compagnie); CA, 107,23343
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