bietaserpine Chemical Properties

alpha 

D17 -121° (c = 2 in CHCl3)

Boiling point:

706.92°C (rough estimate)

Density 

1.1581 (rough estimate)

refractive index 

1.7800 (estimate)

bietaserpine Usage And Synthesis

Originator

Tensibar,Lefranco,France,1967

Definition

ChEBI: (1R,15S,17R,18R,19S,20S)-3-[2-(diethylamino)ethyl]-6,18-dimethoxy-17-[oxo-(3,4,5-trimethoxyphenyl)methoxy]-11,12,14,15,16,17,18,19,20,21-decahydro-1H-yohimban-19-carboxylic acid methyl ester is a yohimban alkaloid.

Manufacturing Process

The first stage is to prepare the naphthyl sodium solution in the following way:
To a solution of 0.6 g naphthalene in 10 ml tetrahydrofurane, anhydrous, used as solvent, add 96 mg sodium under a nitrogen atmosphere. After a few minutes, an intensive dark green coloration develops, while the sodium dissolves. The reaction is completed after a period of time ranging between 30 and 60 minutes.
Then add to the above solution a solution of 2.42 g reserpine in 60 ml anhydrous dioxan at 50°C.
After heating for 15 minutes (which corresponds to carrying out reaction a), add 0.6 g, diethylaminochloroethane, while the mixture is kept boiling under reflux, for 6 hours. Reaction b is then completed.
Then cool the mixture and evaporate the dioxan under reduced pressure. The pasty residue is dissolved in a mixture of 50 ml benzene and 20 ml ether, and washed several times with water.
The aqueous solutions resulting from the washing are also extracted with ether, and the ether portions are added to the main ether-benzene solution. This solution is extracted several times with 5% acetic acid, until the silicotungstate test (an identification test for alkaloids) yields a negative result, and the acetic solutions are washed with 10 ml ether.
After combining the acetic extracts, the solution is adjusted to a pH of 9 with sodium carbonate, which precipitates the base, which is insoluble in water. The oily suspension obtained in this way is extracted several times with chloroform. The chloroform solutions are then washed, each with 10 ml water, then they are combined and dried over anhydrous potassium carbonate.
After filtering and evaporating the solvent under reduced pressure, the pasty residue, constituted by the enriched product, is diluted with 30 ml ether and in this way 0.225 g reserpine (which has not taken part in the reaction) is isolated by filtration.
After evaporation of the ether under reduced pressure, 1.525 g of the crude resinous base is obtained, which constitutes the required product in a crude and impure condition.
This product is purified in the following way: After dissolving in 15 ml of dry benzene, the resulting solution is filtered on an alumina column, which fixes the base.
After consecutive elutions with pure benzene, and benzene containing increasing proportions of chloroform,0.748 g of 1-diethylaminoethylreserpineis isolated in the form of a resin. The crystalline acid bitartrate prepared in ethyl acetate melts at 145°-150°C, with decomposition.

Therapeutic Function

Antihypertensive

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