BAMIPINE

Originator

Bamipine,Pharm Chemical

The Uses of BAMIPINE

Bamipine is an antihistamine that has anticholinergic properties. It is also a reagent for dopamine D3 receptor ligands based on scaffolds of biogenic amine GPCR (G protein-coupled receptor) ligands.

Definition

ChEBI: Bamipine is an aromatic amine.

Manufacturing Process

80 g of 1-methyl-piperidone-4 and 70 g of aniline are boiled, using a water separator in 350 ml of toluene to which several drops of glacial acetic acid have been added, until the theoretical quantity of water (12.7 ml) has separated out. The toluene is then distilled off and the remains are fractionated at reduced pressure. At a boiling point of 156°C/13 mm of Hg pressure, 118 g of a weakly yellow colored oil of the anil of 1-methyl-1- piperidone-4 are obtained.
100 g of the above described anil of 1-methyl-1-piperidone-4 are boiled for 8 hours, using a reflux condenser, with 30 g of activated borings of aluminum in 300 ml of methanol diluted with 60 ml of water. The liquid phase is then separated from the solid phase, the solvent is evaporated and the residuum is fractionated at reduced pressure, 95 g of a colorless oil being obtained boiling at 163-165°C at 15 mm of Hg pressure. The oil solidifies at once to a mass of crystals of 4-N-phenylaimno-1-methylpiperidine. After having been recrystallized from dibutyl ether the base melts at 87°C, its dihydrochloride has the melting point of 246°C.
95 g of 4-N-phenylamino-1-methylpiperidine are boiled together with 22 g of pulverized sodium amide in 300 ml of benzene, using a reflux condenser, while nitrogen is passed through the reaction mixture, until the evolution of ammonia has ceased. 64 g of benzyl chloride are then gradually added drop by drop to the boiling reaction product and boiling is continued for several hours. After having been cooled the solution is shaken with water and subsequently dried with potassium carbonate. The solvent having been evaporated the remaining base of 4-(N-phenyl-N-benzyl)-amino-1- methylpiperidine solidifies with the formation of crystals, the yield amounting to 123 g. The base is recrystallized from dibutyl ether and has a melting point of 115°C; its dihydrochloride melts at 189°C.

Therapeutic Function

Antihistaminic, Antiallergic