caroxazone Struktur

Caroxazon

Bezeichnung:Caroxazon

CAS-Nr18464-39-6

Englisch Name:caroxazone

CBNumberCB3937510

SummenformelC10H10N2O3

Molgewicht206.2

MOL-Datei18464-39-6.mol

Synonyma

Caroxazon

Caroxazon physikalisch-chemischer Eigenschaften

Schmelzpunkt	203-205°
Siedepunkt	435.1±45.0 °C(Predicted)
Dichte	1.345±0.06 g/cm3(Predicted)
pka	15.73±0.40(Predicted)

Sicherheit

RIDADR	3249
HazardClass	6.1(b)
PackingGroup	III

caroxazone Chemische Eigenschaften,Einsatz,Produktion Methoden

Originator
Timostenil,Farmitalia,Italy,1975
Verwenden
Caroxazone acts as an irreversible, nonselective MAO inhibitor, displaying antidepressant characteristics.
Definition
ChEBI: Caroxazone is a benzoxazine.
Manufacturing Process
37.9 g of ethyl glycinate hydrochloride were dissolved in 400 cc of ethanol and 33.5 g of salicylic aldehyde were added. It is refluxed for half an hour and cooled. 38 cc of triethylamine and 25 g of Raney nickel are then added where after hydrogenation is carried out at room temperature and under atmospheric pressure. After hydrogen adsorption was complete, the mixture was filtered and the alcohol evaporated off. The residue was taken up with acidified water, extracted with ether to eliminate part of the by-products, consisting mainly of o-cresol, then made alkaline with ammonia and extracted with ethyl acetate. The solvent was removed in vacuo and the residue crystallized from ether/petroleum ether. 36.7 g of o-hydroxybenzylaminoacetic acid ethyl ester melting at 47°C are obtained.
20 g of this compound were dissolved in 100 cc of tetrahydrofuran and 100 cc of a 30% solution of phosgene in tetrahydrofuran solution were added. After one night at room temperature, the reaction mixture was dried, taken up with 150 cc of anhydrous pyridine and allowed to stand overnight. The pyridine was then removed in vacuo and the residue dissolved in benzol was washed several times with water and chromatographed over 250 g of alumina. Elution with benzene/petroleum ether yielded 16 g of 4H-3-carboethoxymethyl-1,3- benzoxazine-2-one, melting at 90°-91°C.
5 g of this last compound were dissolved in 120 cc of absolute ethanol and saturated with NH3 at 0°C. It was allowed to stand overnight where after 1.5 g of 4H-3-carboxamidomethyl-1,3-andenzoxazine-2-one, melting at 205°C, were obtained. By evaporation from the mother liquors further quantities of the same product were obtained.
Therapeutic Function
Antidepressant

caroxazone Upstream-Materialien And Downstream Produkte

Caroxazon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

18464-39-6, caroxazone Verwandte Suche:

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