26615-21-4 Usage
Chemical Properties
White to off white crystalline powder
Originator
Lodopin,Fujisawa Pharmaceutical,Japan,1982
Manufacturing Process
A suspension of 30 g of sodium hydride in benzene (30 ml) was added
dropwise to 52 g of 8-chlorodibenzo[b,f]thiepin-10(11H)-one dissolved in
dimethylformamide (800 ml), and the mixture was heated at 100°C for 2
hours. To this, there were added 68 g of 2-dimethylaminoethyl chloride, and
the mixture was heated at 60°C for 39 hours. The reaction mixture, after
cooled, was poured into ice-water, and the solution was extracted with ethyl
acetate. The ethyl acetate layer, after washed with water, was extracted with
10% hydrochloric acid, when oil was precipitated. The aqueous layer, in which
oil was precipitated, was washed with ether, made neutral with concentrated
sodium hydroxide solution and then extracted with ethyl acetate. The ethyl
acetate layer was washed with water, dried over magnesium sulfate, and
concentrated to give oil, which was allowed to stand to provide solid. The solid
was washed with petroleum ether and recrystallized from cyclohexane to yield
42.5 g of 8-chloro-10-(2-dimethylaminoethyl)-oxydibenzo[b,f]thiepin as
crystals, melting point 90°C to 91°C. Maleate as colorless needle, melting
point 204°C to 204.5°C.
Therapeutic Function
Tranquilizer
Check Digit Verification of cas no
The CAS Registry Mumber 26615-21-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,6,1 and 5 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 26615-21:
(7*2)+(6*6)+(5*6)+(4*1)+(3*5)+(2*2)+(1*1)=104
104 % 10 = 4
So 26615-21-4 is a valid CAS Registry Number.
InChI:InChI=1/C18H18ClNOS/c1-20(2)9-10-21-16-11-13-5-3-4-6-17(13)22-18-8-7-14(19)12-15(16)18/h3-8,11-12H,9-10H2,1-2H3
26615-21-4Relevant articles and documents
Synthesis and oxidant properties of phase 1 benzepine N-oxides of common antipsychotic drugs
Koerber, Jochen,Loeffler, Stefan,Schollmeyer, Dieter,Nubbemeyer, Udo
, p. 2875 - 2887 (2013/10/22)
There is increasing evidence that cell constituents are oxidized by widely used antipsychotic drugs but until now the underlying chemistry has remained unclear. It is well known that such drugs readily undergo N-oxidation as a first key metabolic step. To gain insight into the problem, the tertiary phase 1 N-oxides of clozapine, olanzapine, quetiapine, and zotepine were synthesized, together with the N,S-dioxides of quetiapine and zotepine. These N-oxides were then subjected to well-established chemical transformations to test their oxidant properties in group VIII transition-metal-catalyzed reactions. In the osmium tetroxide catalyzed dihydroxylation of styrene or cinnamyl alcohol and in the tetrapropylammonium perruthenate catalyzed oxidation of cinnamyl alcohol, the benzepine N-oxides could be used as replacements for the standard oxidant, N-methylmorpholine N-oxide (NMO) with varying degrees of efficiency. From a chemical point of view, clozapine N-oxide displayed a comparable oxidation power to NMO, characterizing the benzepines as oxygen carriers. Moreover, quetiapine was found to be an excellent double oxygen acceptor, undergoing initial N-oxidation and subsequent S-oxidation. It is therefore worthwhile considering whether oxidative damage to the human body might be related to the potential redox properties of common antipsychotic drugs. Georg Thieme Verlag Stuttgart ? New York.
Synthesis and pharmacological properties of 8-chloro-10-(2-dimethylamino-ethoxy)dibenzo[b,f]thiepin and related compounds. Neurotropic and psychotropic agents. III
Ueda,Sato,Maeno,Umio
, p. 3058 - 3070 (2007/10/05)
-
