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

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

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

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.

Preparation of physostigmine carbamate derivatives from physostigmine

This application relates to a new process for the preparation of a product of the formula STR1 wherein R, R1, R2, X and m are as defined within, which process comprises preparing treating a compound such as physostigmine to form eseroline which is then treated with an appropriate compound or its equivalent. Acetic acid is added to the reaction mixture after the formation of eseroline.

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.