viquidil

Originator

Desclidium,Spret ,France,1972

The Uses of viquidil

1-(6-Methoxyquinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)propan-1-one (CAS# 84-55-9) is in intermediate in the synthesis of Quinotoxine Hydrochloride (Q753500), an isomer of quinine; occurs naturally as the d-form. Present in small quantities in cinchona barks. Vasodilator (cerebral).

Definition

ChEBI: Viquidil is a member of quinolines.

Manufacturing Process

2.70 g of N-benzoylhomomeroquinene ethyl ester (0.0086 mol) are mixed with 4.0 g of ethyl quininate (0.0173 mol = 100% excess). 1.4 g of absolutely dry pulverulent sodium ethoxide (0.0207 mol -140% excess, based on N- benzoylhomomeroquinene ethyl ester) is added, and the reaction mixture is heated to about 80°C with continuous stirring. As the ethyl quininate melts, and the materials become thoroughly mixed, the initial yellow color changes to brown and then gradually to deep red. The reaction mixture is maintained at about 82°C for fourteen hours with continuous stirring. It is then cooled, and the resulting very hard, dark red mass is decomposed with ice water and benzene. The (not entirely clear) combined aqueous layers are extracted with a small amount of ether. The clear, deep red, aqueous layer is then made just acid to litmus. The precipitated oil is taken up in ether. Evaporation of solvent, finally in vacuo, gives 2.56 g of a red glass. The combined benzene and ether extracts from above, containing largely neutral material, are extracted with 10% aqueous sodium hydroxide. The alkaline extract is made just acid to litmus, and extraction with ether followed by removal of solvent gives a further small quantity of β-ketoester, 0.16 g.
Total weight of N-benzoylquinotoxine carboxylic acid ethyl ester thus obtained was 2.72 g, equivalent to 63.4% of the theoretical.
2.72 g of N-benzoylquinotoxine carboxylic acid ethyl ester are dissolved in 30 cc of 1:1 aqueous hydrochloric acid (from 15 cc concentrated hydrochloric acid and 15 cc water). The clear, reddish-orange solution is then boiled under reflux for four hours. The very dark reddish-brown solution is extracted with ether (from this extract 0.50 g of benzoic acid is obtained on evaporation). The aqueous solution is then made strongly alkaline and extracted with ether. 0.23 g of ether-insoluble interface material is dissolved in benzene and set aside. Removal of solvent from the above ether extract gives 1.39 g of crude quinotoxine as a dark red viscous oil.

Therapeutic Function

Vasodilator, Antiarrhythmic