Alkylenediamine derivatives

#1. Field of the Invention

#The present invention relates to novel alkylenediamine derivatives. The alkylenediamine derivatives of the invention are favorably employable as glutamate blockers.

#2. Description of Prior Art

#The present invention is further described by the following examples.

#i) A mixture of 2.47 g of 5-methyl-2-phenylhexanoic acid and 1.43 g of thionyl chloride was stirred at room temperature for 27 hours, and subsequently excessive thionyl chloride was distilled off under reduced pressure at temperatures of lower than 40.degree. C. The residue was dissolved in 5 mi of benzene. To the benzene solution was dropwise added under chilling with ice and vigorous stirring over a period of 15 min. a mixture of 50 ml of 1N aqueous sodium hydroxide and a solution of 1.42 g of 1-(3-aminopropyl)piperidine in 50 ml of chloroform. The stirring was continued for 30 min. under chilling with ice and for 40 min. at room temperature. The organic layer was separated and washed successively with water and saturated aqueous sodium chloride. The organic layer was then dried over anhydrous sodium sulfate and evaporated under reduced pressure to remove the solvent. There was obtained 3.0 g of 5-methyl-2-phenyl-N-(3-piperidinopropyl)hexanamide as a viscous oil, yield: 90.9%.

#ii) To a solution of 3.0 g of the above-obtained product in 80 ml of ether was added 0.69 g of aluminum lithium hydride, and the resulting mixture was heated under reflux for 20 hours. To the reaction mixture was dropwise added under chilling with ice a saturated aqueous sodium sulfate solution to decompose an excessive portion of the aluminum lithium hydride. The insolubles were then removed by decantation. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to remove the solvent, yielding an oily product. The oily product was purified by silica gel column chromatography (eluent: chloroform-methanol) to give 2.6 g of the desired compound.