Perithiaden

---

Perithiaden

Identifiers
IUPAC name 4-(6H-benzo[c][1]benzothiepin-11-ylidene)-1-methylpiperidine
CAS Number	1447-70-7
PubChem CID	121108
ChemSpider	108103
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C20H21NS
Molar mass	307.46 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1CCC(=C2C3=CC=CC=C3CSC4=CC=CC=C42)CC1
InChI InChI=InChI=1S/C20H21NS/c1-21-12-10-15(11-13-21)20-17-7-3-2-6-16(17)14-22-19-9-5-4-8-18(19)20/h2-9H,10-14H2,1H3 Key:MBGXTYVKSKOCFX-UHFFFAOYSA-N

Perithiaden is from the dibenzothiepin family of agents.

It is useful as sedative-neuroleptic, muscle-relaxant and sleep-promoting agent.

This compound is very similar in structure to both dothiepin as well as pimethixene, which is the six membered ring version of perithiadene. The relative rigidity of the piperidine ring as well as the olefinic bridge that can covalently bind to the receptor would both be expected to affect the activity. The SAR is also related to pipethiaden.

Synthesis

Perithiaden synthesis

4-Chloro-N-methylpiperidine is converted to a Grignard reagent with magnesium and is then reacted with dibenzo[b,e]thiepin-11(6H)-one to convert the ketone to a tertiary alcohol. The tertiary alcohol is then dehydrated by an acid to the olefin that is Perthiaden.

References

This article "Perithiaden" is from Wikipedia. The list of its authors can be seen in its historical and/or the page Edithistory:Perithiaden. Articles copied from Draft Namespace on Wikipedia could be seen on the Draft Namespace of Wikipedia and not main one.

---