139314-01-5

Basic information

• Product Name: Quilostigmine
• Synonyms: Quilostigmine
• CAS NO: 139314-01-5
• Molecular Formula: C23H27N3O2
• Molecular Weight: 377.47938
• Mol File: 139314-01-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 535.7°Cat760mmHg
• Flash Point: 277.8°C
• Appearance: /
• Density: 1.215g/cm³
• Vapor Pressure: 1.5E-11mmHg at 25°C
• Refractive Index: 1.617
• CAS DataBase Reference: Quilostigmine(CAS DataBase Reference)
• NIST Chemistry Reference: Quilostigmine(139314-01-5)
• EPA Substance Registry System: Quilostigmine(139314-01-5)

Safety Data

• Hazardous Substances Data: 139314-01-5(Hazardous Substances Data)

Usage

Uses

Quilostigmine is an acetylcholinesterase inhibitor used for Alzheimer''s disease treatment.

InChI:InChI=1/C23H27N3O2/c1-23-11-13-24(2)21(23)25(3)20-9-8-18(14-19(20)23)28-22(27)26-12-10-16-6-4-5-7-17(16)15-26/h4-9,14,21H,10-13,15H2,1-3H3/t21-,23+/m1/s1

Upstream product

• 57-47-6 Physostigmin 
• 530-62-1 1,1'-carbonyldiimidazole 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 469-23-8 (3AS-cis)-5-ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indole 
• 65166-97-4 (-)-esermethole 
• 469-22-7 eseroline 

Relevant articles and documents

An efficient O-dealkylation procedure for the synthesis of (3aS,cis)- 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-yl-3,4-dihydro- 2(1H)-isoquinolinecarboxylate

The title compound is synthesized in high yields and purity from (-)- eserethole (2a) via a lithium bromide catalyzed hydrobromic acid O- dealkylation procedure as the key step.

Method of preparation of physostigmine carbamate derivatives from eseretholes

This application relates to a new process for the preparation of a product of the formula STR1 wherein R is loweralkyl; R1 is hydrogen, loweralkyl, lowercycloalkyl, lowercycloalkylloweralkyl, lowerbicycloalkyl, aryl or arylloweralkyl; R2 is loweralkyl, lowercycloalkyl, lowercycloalkylloweralkyl, lowerbicycloalkyl, aryl or arylloweralkyl; or R1 and R2 taken together with the nitrogen atom to which they are attached from a 3,4-dihydro-2H(1H)-isoquinoline group; X is loweralkyl, loweralkoxy, halogen or trifluoromethyl; and m is 0, 1 or 2; which process comprises (a) contacting a compound of formula II STR2 wherein R, X and m are as defined above and R3 is loweralkyl, with aluminum chloride followed by tartaric acid to afford a compound of formula III STR3 wherein R, X and m are as defined above; (b) contacting the reaction mixture containing the compound of Formula III either (1) with an isocyanate of the formula R1 NCO and obtaining a product of the formula I wherein R2 is hydrogen; or (2) with a compound of formula IV STR4 wherein R4 is hydrogen or loweralkyl in the presence of a carboxylic acid of the formula wherein R5 is loweralkyl to afford a compound of formula V STR5 wherein R, R4, X and m are as above; contacting the reaction mixture containing the compound of Formula V with a compound of the formula wherein R1 and R2 are as above; and isolating the product of Formula I.