130953-69-4

Basic information

• Product Name: besipirdine
• Synonyms: besipirdine;1H-Indol-1-amine, N-propyl-N-4-pyridinyl-, monohydrochloride;Besipirdine HCl;Besipirdine hydrochloride;HP 749;ZDFVWDHZXAGROF-UHFFFAOYSA-N
• CAS NO: 130953-69-4
• Molecular Formula: C16H17N3.ClH
• Molecular Weight: 287.792
• Mol File: 130953-69-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 212-214°
• Boiling Point: 405.9°Cat760mmHg
• Flash Point: 199.3°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 8.49E-07mmHg at 25°C
• CAS DataBase Reference: besipirdine(CAS DataBase Reference)
• NIST Chemistry Reference: besipirdine(130953-69-4)
• EPA Substance Registry System: besipirdine(130953-69-4)

Safety Data

• Hazardous Substances Data: 130953-69-4(Hazardous Substances Data)

Usage

Originator

Besipirdine,Hoechst-Roussel

Manufacturing Process

Part A: N-Propyl-N-(4-pyridinyl)-1H-indol-1-amine maleate: A solution of N-(4-pyridinyl)-1H-indol-1-amine (6 g) in 25 ml of dimethylformamide was slowly added to an ice-cooled suspension of NaH (1.3 g of 60% NaH dispersion in mineral oil was washed with hexanes, the liquid was decanted and the residual solid was dispersed in 5 ml of dimethylformamide). After anion formation, a solution of 1-bromopropane (4 g) in 5 ml of dimethylformamide was added. After one hour of stirring at ambient temperature, the reaction mixture was stirred with ice-water and extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride solution, was dried over anhydrous magnesium sulfate, filtered and concentrated to 8 g of oil. This oil was purified by HPLC (silica, ethyl acetate) and thereafter by column chromatography (alumina, ether) to give 6.4 g oil. This oil was converted to the maleate salt and recrystallized from methanol/ether to give 6.8 g of crystals, m.p. 115-116°C. Part B: N-Propyl-N-(4-pyridinyl)-1H-indol-1-amine hydrochloride: N-Propyl-N-(4-pyridinyl)-1H-indol-1-amine maleate was converted to the free base by action of alcaline agent. Then the free base oil was converted to the hydrochloride salt which was recrystallized from methanol; m.p. 212-214°C.

Therapeutic Function

Cognition activator

InChI:InChI=1/C16H17N3.ClH/c1-2-12-18(15-7-10-17-11-8-15)19-13-9-14-5-3-4-6-16(14)19;/h3-11,13H,2,12H2,1H3;1H

Relevant articles and documents

USE OF UNSUBSTITUTED AND SUBSTITUTED N-(PYRROL-1-YL)PYRIDINAMINES AS ANTICONVULSANT AGENTS

This invention relates to a method of treating a patient in need of relief from convulsions which comprises administering to such a patient a convulsion-alleviating amount of a compound of formula (I), wherein R, R, R, R, R, m and n are as def

Use of N-(pyridinyl)-1H-indol-1-amines for the treatment of obsessive-compulsive disorder

There is disclosed a method of alleviating obsessive compulsive disorders which comprises administration of an effective amount of a compound of the formula. STR1 where m is 1 or 2; R is H, halogen, loweralkyl, loweralkoxy, arylloweralkoxy, hydroxy, nitro, amino, loweralkylamino or diloweralkylamino; R1 is H or loweralkyl; R2 is H or loweralkyl; and R3 is H, halogen or loweralkyl.