The present invention concerns new cationic quaternary ammonium compounds which exhibit excellent adsorption properties on negatively charged surfaces. These ones can notably be obtained firstly by reacting an internal ketone with a twin-tail amine under reductive amination conditions to obtain a twin tail triamine, then subjecting the twin tail triamine to a quaternization reaction. They can also obtained be obtained by the quaternization reaction of a certain diamine.

The present invention concerns new cationic quaternary ammonium compounds which exhibit excellent adsorption properties on negatively charged surfaces. These ones can notably be obtained firstly by reacting an internal ketone with a twin-tail amine under reductive amination conditions to obtain a twin tail triamine, then subjecting the twin tail triamine to a quaternization reaction. They can also obtained be obtained by the quaternization reaction of a certain diamine.

It is provided a method of converting a diaryl ether source such as lignin and/or polyphenylene oxide (PPO) containing 4-O-5 linkages and an inorganic chemical such as ammonia into an organic compound, comprising reacting said diaryl ether source with the inorganic chemical in presence of a catalyst, preferably palladium, transforming the 4-O-5 linkages of said diaryl ether source into the organic compound. It is provided a palladium-catalyzed synthesis of aniline derivatives from 4-O-5 linkage lignin model compounds and cheap industrial inorganic chemical ammonia via dual C(Ar)O bond cleavage.

It is provided a method of converting a diaryl ether source such as lignin and/or polyphenylene oxide (PPO) containing 4-O-5 linkages and an inorganic chemical such as ammonia into an organic compound, comprising reacting said diaryl ether source with the inorganic chemical in presence of a catalyst, preferably palladium, transforming the 4-O-5 linkages of said diaryl ether source into the organic compound. It is provided a palladium-catalyzed synthesis of aniline derivatives from 4-O-5 linkage lignin model compounds and cheap industrial inorganic chemical ammonia via dual C(Ar)O bond cleavage.

A new family of therapeutics which provides a controlled-release delivery platform for non-steroidal anti-inflammatory agents on an ester or an ester-carbonate backbone is disclosed herein. These agents are reversible inhibitors of acetylcholinesterase and are thus useful for clinical conditions benefiting from inflammation suppression and cholinergic intervention. These compounds are of the general formula wherein n=0, 1; X=C, Si, and N+ and NSAID=ibuprofen, naproxen, indomethacin and diclofenac. Other embodiments are also disclosed. ##STR00001##

A direct reductive amination of aldehydes, ketones, and keto acids with trifluoroacetoxyborane-amines (TFAB-amines), which are mild reductive amination agents prepared by monoacetoxylation of borane-amines; Aromatic and aliphatic lactams are obtained via a tandem reductive amination-cycloamidation of keto acids using TFAB-amine.

A direct reductive amination of aldehydes, ketones, and keto acids with trifluoroacetoxyborane-amines (TFAB-amines), which are mild reductive amination agents prepared by monoacetoxylation of borane-amines; Aromatic and aliphatic lactams are obtained via a tandem reductive amination-cycloamidation of keto acids using TFAB-amine.

Methods of preparing a fenfluramine active pharmaceutical ingredient are provided. Aspects of the method include (a) hydrolyzing a 2-(3-(trifluoromethyl)phenyl)acetonitrile composition to produce a 2-(3-(trifluoromethyl)phenyl)acetic acid composition; (b) reacting the 2-(3-(trifluoromethyl)phenyl)acetic acid composition with acetic anhydride and a catalyst to produce a 1-(3-(trifluoromethyl)phenyl)propan-2-one composition; and

(c) reductively aminating the 1-(3-(trifluoromethyl)phenyl)propan-2-one composition with ethylamine using a borohydride reducing agent to produce a fenfluramine composition. Also provided are compositions and pharmaceutical ingredients prepared according to the subject methods including a pharmaceutically acceptable salt of fenfluramine and having less than 0.2% by weight in total of trifluoromethyl regioisomers.

Methods of preparing a fenfluramine active pharmaceutical ingredient are provided. Aspects of the method include (a) hydrolyzing a 2-(3-(trifluoromethyl)phenyl)acetonitrile composition to produce a 2-(3-(trifluoromethyl)phenyl)acetic acid composition; (b) reacting the 2-(3-(trifluoromethyl)phenyl)acetic acid composition with acetic anhydride and a catalyst to produce a 1-(3-(trifluoromethyl)phenyl)propan-2-one composition; and

(c) reductively aminating the 1-(3-(trifluoromethyl)phenyl)propan-2-one composition with ethylamine using a borohydride reducing agent to produce a fenfluramine composition. Also provided are compositions and pharmaceutical ingredients prepared according to the subject methods including a pharmaceutically acceptable salt of fenfluramine and having less than 0.2% by weight in total of trifluoromethyl regioisomers.

Methods of preparing a fenfluramine active pharmaceutical ingredient are provided. Aspects of the method include (a) hydrolyzing a 2-(3-(trifluoromethyl)phenyl)acetonitrile composition to produce a 2-(3-(trifluoromethyl)phenyl)acetic acid composition; (b) reacting the 2-(3-(trifluoromethyl)phenyl)acetic acid composition with acetic anhydride and a catalyst to produce a 1-(3-(trifluoromethyl)phenyl)propan-2-one composition; and

(c) reductively aminating the 1-(3-(trifluoromethyl)phenyl)propan-2-one composition with ethylamine using a borohydride reducing agent to produce a fenfluramine composition. Also provided are compositions and pharmaceutical ingredients prepared according to the subject methods including a pharmaceutically acceptable salt of fenfluramine and having less than 0.2% by weight in total of trifluoromethyl regioisomers.