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- Intermediates & Fine Chemicals
- Pfizer Compounds
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Avridine Chemical Properties
- storage temp.
- Store at RT
- DMSO: ≥5mg/mL (with warming to 60 °C for 5 minutes)
- white to off-white
Avridine Usage And Synthesis
Off-White to Pale Yellow Solid
A potent synthetic non-immunogenic adjuvant that can induce arthritis in most rat strains; immunomodulator and interferon-inducing.
A). A two-gallon autoclave is charged with 3-(dioctadecylamino)propionitrile (100 g), ethanol (3750 ml) containing anhydrous ammonia (100 g) and Raney nickel (20 g dry basis) and purged with nitrogen, then with hydrogen. It is then sealed and the hydrogen pressure raised to 250 psi. The autoclave is agitated, the temperature raised to 70°C and the mixture held at this temperature for 1.5 hours at which time hydrogen absorption has ceased. The autoclave is cooled to 20°C, vented, and the contents removed. The catalyst is filtered off, washed with ethanol, and the combined washings and reaction mixture concentrated in vacuum to a viscous green-yellow oil (82 g) which solidified upon standing, MP: 39°-41°C.
3-(Dioctadecylamino)propionitrile is prepared by refluxing a mixture of dioctadecylamine (200 g) and acrylonitrile (1903.8 ml) for eighteen hours. The mixture is then concentrated to a waxy semi-solid which is slurried in acetone, filtered, and air dried overnight.
B). The monoacyl derivatives of N,N-dioctadecyl-1,3-propanediamine are prepared as follows:
To a solution of methylene chloride (500 ml per 0.1 mole of reactants) containing equimolar amounts of N,N-dioctadecyl-1,3-propanediamine and triethylamine and cooled in an ice-bath is added an equimolar amount of the appropriate acyl chloride in methylene chloride (25 ml per 0.1 mole of acyl chloride) over a period of 15 minutes. The mixture is stirred for ten minutes then brought to room temperature and stirred for one hour. The methylene chloride phase is separated and extracted with water (3x25 ml). The water is in turn extracted with methylene chloride (2x25 ml) and the combined methylene chloride phases dried (Na2SO4) then evaporated under reduced pressure. The residue is taken up in benzene and the solution passed through a silica gel column. The column is eluted with benzene, then with benzene containing increasing amounts of ethyl acetate, e.g., 5, 10, 25, and 50 %. The eluate is subjected to thin layer chromatography (ethyl acetate) and those fractions, which show only one spot, combined and evaporated to give N,N-dioctadecyl-N',N'-bis(2-hydroxyethyl)propanediamine M.P. 48.5°-49°C.
Non-immunogenic adjuvant; used to induce arthritis in Lewis (LEW) and DA rats.
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