Originator
Dactil, Merrell National ,US ,1954
Manufacturing Process
To obtain the free base, 34 g (0.256 mol) of N-ethyl-3-piperidinol and 20 g (0.22 mol) of diphenylacetyl chloride were mixed in 80 cc of isopropanol and the solution was refluxed for 2 hours. The isopropanol was evaporated in vacuo at 30 mm pressure, the residue was dissolved in 150 cc of water and the aqueous solution was extracted several times with ether. The aqueous solution was then neutralized with potassium carbonate and extracted withether. The ethereal solution was dried over anhydrous potassium carbonate and the ether removed by distillation. The product was then distilled at its boiling point 180° to 181°C at 0.13 mm of mercury whereby 14 g of a clear yellow, viscous liquid was obtained. The nitrogen content for C21H25NO2 was calculated as 4.33% and the nitrogen content found was 4.21%.
The starting material was produced by the reaction of furfural with ethylamine followed by hydrogenation to give N-ethyl-N-(2-tetrahydrofurfuryl)amine. Treatment of that material with hydrogen bromide in acetic acid gives N-ethyl3-piperidinol.
