59338-93-1

Basic information

• Product Name: Alizapride
• Synonyms: ALIZAPRIDE;n-(1-allyl-2-pyrrolidinylmethyl)-6-methoxy-1h-benzotriazole-5-carboxamide;1h-benzotriazole-5-carboxamide,6-methoxy-n-((1-(2-propenyl)-2-pyrrolidinyl)met;6-methoxy-n-((1-(2-propenyl)-2-pyrrolidinyl)methyl)-1h-benzotriazole-5-carbo;6-Methoxy-N-{[1-(2-propnyl)-2-pyrrolidinyl]methyl]-1H-benzotriazole-5-carboxamide;Litican;Nausilen;Plitican
• CAS NO: 59338-93-1
• Molecular Formula: C₁₆H₂₁N₅O₂
• Molecular Weight: 315.37
• EINECS: 261-710-6
• Mol File: 59338-93-1.mol
• Article Data: 0

Chemical Properties

• Melting Point: 139°
• Boiling Point: 580.3 °C at 760 mmHg
• Flash Point: 304.8 °C
• Appearance: /
• Density: 1.224 g/cm³
• Vapor Pressure: 1.47E-14mmHg at 25°C
• Storage Temp.: 2-8°C(protect from light)
• PKA: 7.09±0.40(Predicted)
• CAS DataBase Reference: Alizapride(CAS DataBase Reference)
• NIST Chemistry Reference: Alizapride(59338-93-1)
• EPA Substance Registry System: Alizapride(59338-93-1)

Safety Data

• Hazardous Substances Data: 59338-93-1(Hazardous Substances Data)

Usage

Originator

Plitican ,Delagrange ,France ,1981

Manufacturing Process

38.6 g (0.2 mol) of 2-methoxy-4,5-azimidobenzoic acid were dissolved in anhydrous toluene and 56 g (0.4 mol) of 1-allyl-2-amino-methylpyrrolidine were added. The mixture was heated to 50°C and then 42 g (0.3 mol) of phosphoric anhydride were added. The mixture was warmed at reflux temperature for 3 hours and then cooled to 80°C. After adding water, the aqueous layer was alkalized. The crystals were filtered, washed with water and then dissolved in 450 ml of acetone. After crystallization, the product was 40.4 g (yield 65%) of N-(1'-allyl-2'-pyrrolidylmethyl)-2-methoxy-4,5- azimidobenzamide having a melting point of 139°C were obtained.

InChI:InChI=1/C16H21N5O2.ClH/c1-3-6-21-7-4-5-11(21)10-17-16(22)12-8-13-14(19-20-18-13)9-15(12)23-2;/h3,8-9,11H,1,4-7,10H2,2H3,(H,17,22)(H,18,19,20);1H

Synthetic route

alizapride (59338-93-1) → N-<(1-allyl-2-pyrrolidinyl)methyl>-6-hydroxy-1H-benzotriazole-5-carboxamide (114614-65-2)

Conditions	Yield
With sodium hydride; ethanethiol In N,N-dimethyl-formamide at 100 - 105℃; for 1.5h;	46%

alizapride (59338-93-1) → 6-methoxy-1H-benzotriazole-5-carboxylic acid (59338-92-0)

Conditions	Yield
With hydrogenchloride In water at 80℃; Thermodynamic data; Kinetics; Rate constant; hydrolysis constants by the action of 1M NaOH(aq.), t0.5, other temperatures, ΔG(excit.);

alizapride (59338-93-1) → N-<(1-allyl-2-pyrrolodinyl)methyl>-6-(1-methyl-2-oxopropoxy)-1H-benzotriazole-5-carboxamide (114614-67-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 46 percent / sodium hydride, ethanethiol / dimethylformamide / 1.5 h / 100 - 105 °C 2: 2.) K2CO3, NaI / 1.) DMF, 3 h, 2.) room temperature, 16 h 3: 19 percent / aq. HCl / methanol / 0.17 h / 60 °C View Scheme

alizapride (59338-93-1) → 5-[(1-Allyl-pyrrolidin-2-ylmethyl)-carbamoyl]-6-(1-methyl-2-oxo-propoxy)-benzotriazole-1-carboxylic acid tert-butyl ester (114614-66-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 46 percent / sodium hydride, ethanethiol / dimethylformamide / 1.5 h / 100 - 105 °C 2: 2.) K2CO3, NaI / 1.) DMF, 3 h, 2.) room temperature, 16 h View Scheme

Downstream Products

• 59338-92-0 6-methoxy-1H-benzotriazole-5-carboxylic acid