HCID 86660913, compound → Amantadine

The reaction of the 1-adamantylammonium hydrochloride with aqueous base takes place preferably in the presence of an organic solvent which is water-immiscible and in which the 1-adamantylamine formed dissolves. A water-immiscible organic solvent in the context of the present invention is a solvent which under standard conditions (20° C., 1013 mbar) dissolves to an extent of not more than 10 g in 100 g of water, and in which under standard conditions not more than 10 g of water dissolve in 100 g of solvent. Suitable organic solvents are aromatic hydrocarbons, such as benzene, toluene, ethylbenzene or xylene; halogenated solvents, such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane or chlorobenzene; aliphatic solvents, such as pentane, hexane, heptane, octane, ligroin, petroleum ether, cyclohexane or decalin; and mixtures thereof. Toluene or xylene is preferred. The reaction then takes place as an extractive reaction, the amine liberated undergoing essentially complete transfer to the organic phase. The 1-adamantylamine can be isolated by removing the organic solvent by customary methods, such as evaporation. The evaporation of the solvent may take place in apparatus customary for the purpose. Solvent evaporation takes place preferably under reduced pressure and/or at elevated temperature. For the further reaction it is preferred to use the 1-adamantylamine as a solution in the organic solvent.

ORD record

ord-073523ac81dd4e45945d9d62dd73961b

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772547B2