Oxaflumazine

Originator

Oxaflumine, Diamant ,France,1970

Definition

ChEBI: Oxaflumazine is a member of phenothiazines.

Manufacturing Process

Preparation of N-(3-chloropropyl)-N'-[2-(1,3-dioxanyl)-ethyl]-piperazine: A solution of 30 g (0.15 mol) of N-[2-(1,3-dioxanyl)-ethyl]-piperazine and 11.8 g (0.075 mol) of 1-bromo-3-chloropropane in 150 ml of dry benzene was refluxed with stirring for 5 hours. After cooling, the N-[2-(1,3-dioxanyl)ethyl]-piperazinium bromide which had precipitated was filtered off, the filtrate was concentrated in vacuo and the residual oil was distilled. 14.1 g (68%yield) of N-(3-chloropropyl)-N'-[2-1,3-dioxanyl)-ethyl]-piperazine which occurred as a light yellow oil were obtained. Boiling point: 152°C to 155°C under 0.07 mm Hg (nD23 = 1.4940). The disuccinate prepared in acetone and recrystallized from acetone melts at 104°C to 105°C on a hot stage microscope.
The sodium derivative of the 2-trifluoromethylphenothiazine was prepared from 26.7 g (0.1 mol) of 2-trifluoromethylphenothiazine and 2.3 g (0.1 g atom) of sodium in 500 ml of liquid ammonia. After the reaction was completed, the ammonia was driven off and 500 ml of dry toluene were added. A solution of 25 g (0.09 mol) of N-(3-chloropropyl)-N'-[2-(1,3dioxanyl)-ethyl]-piperazine in 200 ml of toluene was added drop by drop to this solution which was then refluxed with stirring for 18 hours. After cooling, the precipitate which had formed was filtered and the filtrate was washed with water, dried and concentrated in vacuo. 33 g of brown oil, the N-3-(2trifluoromethyl-10-phenothiazinyl)-propyl-N'-2-[2-(1,3-dioxanyl)]-ethylpiperazine, were obtained.
A warm solution of 4.4 g of the base obtained in 100 ml of acetonitrile was added to a warm solution of succinic acid in 200 ml of acetonitrile. After standing for 15 hours at 0°C. the crystalline product was obtained, melting point 138°C.

Therapeutic Function

Neuroleptic, Antihistaminic, Spasmolytic