105601-20-5

Basic information

• Product Name: RIVASTIGMINE
• Synonyms: 3-[1-(Dimethylamino)ethyl]phenyl Ethyl(methyl)carbamate
• CAS NO: 105601-20-5
• Molecular Formula: C₁₄H₂₂N₂O₂
• Molecular Weight: 250.34
• Mol File: 105601-20-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 316.2±34.0 °C(Predicted)
• Appearance: /
• Density: 1.038±0.06 g/cm3(Predicted)
• PKA: 8.62±0.50(Predicted)
• CAS DataBase Reference: RIVASTIGMINE(CAS DataBase Reference)
• NIST Chemistry Reference: RIVASTIGMINE(105601-20-5)
• EPA Substance Registry System: RIVASTIGMINE(105601-20-5)

Safety Data

• Hazardous Substances Data: 105601-20-5(Hazardous Substances Data)

Usage

Uses

(±)-Rivastigmine is a brain selective acetylcholinesterase inhibitor. Nootropic.

Upstream product

• 42252-34-6 N-ethyl-N-methylcarbamoyl chloride 
• 105601-04-5 (+/-)-3-<1-(Dimethylamino)ethyl>phenol 
• 1392101-39-1 3-(1-bromoethyl)phenyl ethyl(methyl)carbamate 
• 124-40-3 dimethyl amine 
• 855300-09-3 1-(N-ethyl-N-methylaminocarbonyloxy)-3-acetylbenzene 
• 1222073-98-4 rac-1-(N-ethyl-N-methylaminocarbonyloxy)-3-(1-hydroxyethyl)benzene 
• 121-71-1 3-Hydroxyacetophenone 
• 624-78-2 N-Ethylmethylamine 
• 50893-53-3 carbonochloridic acid 1-chloro-ethyl ester 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 624-60-2 N-methyl-ethylamine hydrochloride 
• 530-62-1 1,1'-carbonyldiimidazole 
• 90870-20-5 4-nitrophenyl ethyl(methyl)carbamate 
• 948829-23-0 C₁₇H₁₈N₂O₅ 

Downstream Products

• 399515-02-7 (S)-N-ethyl-3-[(1-dimethylamino)ethyl]-N-methylphenylcarbamate di-p-toluoyl-D-tartrate 
• 415973-05-6 (R)-3-(1-(dimethylamino)ethyl) phenylethyl(methyl)carbamate 
• 123441-03-2 rivastigmin 
• 1202748-14-8 R-rivastigmine (-) DPTTA salt 

Relevant articles and documents

A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions

A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.

PROCESS FOR MAKING AMINOALKYLPHENYL CARBAMATES AND INTERMEDIATES THEREFOR

The invention relates to a process for making the compound of general formula (I), or an acid addition salt wherein the dotted line indicates a carbon-carbon bond on the asymmetric carbon, which process comprises the steps of a) the reaction of the compound of formula (II), wherein the dotted line has the same meaning, with bis(p-nitτophenyl)carbonate of the formula (IX) preferably at the temperature between -20 to 50°C and in an inert solvent, followed by b) the reaction of the so formed intermediate of the formula (VII-1) with ethylmethylamine.

AN EFFICIENT METHOD FOR PREPARATION OF (S)-3-[(1-DIMETHYL AMINO)ETHYL]-PHENYL-N-ETHYL-N-METHYL-CARBAMATE

The present invention relates to a method for preparation of substituted phenyl carbamate and pharmaceutically acceptable salts thereof, which are of current pharmaceutical interest. The substituted phenyl carbamate and pharmaceutically acceptable salts thereof are useful to raise cholinergic activity in the central nervous system and useful in treatment of diseases such as Alzheimer's disease, Down's syndrome, Huntingdon's chorea, Friedrich's ataxia etc. (S)-3-[(1-dimethyl amino)ethyl]- phenyl-N-ethyl-N-methyl-carbamate (I) is the active ingredient of the pharmaceutical composition referred in US 5,602,176. This compound is also used to induce selective inhibition of acetylcholinesterase activity in the brain.