Prothipendyl hydrochloride

350 g of dried and cut squill were fermented at 50°C for two hours in 1.1 liters of water. The suspension was then extracted three times with 1.1 liters of ethyl acetate. The extracts were united and evaporated to dryness, the residue was dissolved in 2 ml of dioxaneand chromatographed in a twenty-fold quantity (based on the amount of dried residue) of silica gel. The proscillaridin was then eluated with toluene to which increasing quantities of a methanol-di-oxane mixture were added. The main fraction, containing proscillaridin, was evaporated to dryness. The residue was crystallized out of methanol. Pure proscillaridin was obtained with a melting point of 227°C to 230°C -93.5°C (in methanol). 

The same result was obtained by fermentation on the aqueous suspension of the cut squi room temperature for 24 hours and working up in the manner described. 

Chemical Name N,N-Dimethyl-10H-pyridol3,2-b] (1,4] benzothiazine-10-propanamine hydrochloride 

A mixture of 20 g (0.1 mol) of 1 -azaphenothiazine, 4.3 g (0.11 mol) of sodamide and 300 ml of dry toluene is stirred and refluxed for eight hours. A slow stream of dry nitrogen gas is used to sweep out the ammonia as formed. The mixture is cooled and 110 ml of a 1 M solution of 3-dimethylaminopropyl chloride in toluene is added dropwise, with stirring. Subsequently, the mixture is stirred and refluxed for fifteen hours, cooled, and concentrated in vacuo. The viscous residue is refluxed with 500 ml of chloroform and filtered hot. The chloroform filtrate is treated with activated charcoal and again filtered. The filtrate is concentrated and the residue distilled to give about 19.B g (69% yield) of product, an oil distilling at about 195 C to 19B°C (under 0.5 mm pressure of mercury). 

To a solution of 16.4 g (0.05B mol) of the free base in 75 ml of dry acetonitrile is added dropwise while cooling (ice bath) and stirring 14.5 ml (0.053 mol) of 3.6N ethereal hydrogen chloride. An equal volume of anhydrous ether is addedand the product altered, dried and recrystallized from monochlorobenzene. The product melts at about 177°C to 17B°C with sintering at about 176°C. The yield is about 11.0 g (60%). 

and Bernstein, J. U.S. Patent 2,943,086 June 28,1960 assigned to Olin Mathle-son Chemical Corp. 

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Infra-red Spectrum. Principal peaks at wavenumbers 757, 1295, 780,1592, 1162, 1110 (prothipendyl hydrochloride, KBr disk). 

Prilocaine hydrochloride Primaquine phosphate Procainamide hydrochloride Procaine hydrochloride Procyclidine hydrochloride Progesterone Proguanil hydrochloride Promazine hydrochloride Promethazine hydrochloride Propantheline bromide Prothionamide Prothipendyl hydrochloride Protriptyline hydrochloride Proxyphylline... 

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