139306-10-8

Basic information

• Product Name: 3-[(1S)-1-(Dimethylaminoethyl)]phenol
• Synonyms: 3-[(1S)1-(DIMETHYLAMINO)ETHYL]PHENOL(INTERMEDIATEOFRIVASTIGMINE);(S)-3-(1-N,N-DIMETHY(AMINO)ETHYL PHENOL;(1S)-3-[-1-(Dimethylaminoethyl)]phenol;Rivastigmine-3-(1-(dimethylamino)ethyl)phenol;(S)-3-(1-N,N-dimethylaminoethyl) phenol;(S)-3-1(1-(Dimethylamino)ethylphenol;RivastigMine Metabolite (NAP 226-90);3-[(1(S)-N,N-DiMethylaMino)Ethyl] Phenol
• CAS NO: 139306-10-8
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• EINECS: 1308068-626-2
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Metabolite Reference Standard;Intermediate of Rivastigmine
• Mol File: 139306-10-8.mol
• Article Data: 34

Chemical Properties

• Melting Point: 87-88°C
• Boiling Point: 241℃
• Flash Point: 97℃
• Appearance: off-white to pale yellow crystal
• Density: 1.021
• Vapor Pressure: 0.0233mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.86±0.10(Predicted)
• CAS DataBase Reference: 3-[(1S)-1-(Dimethylaminoethyl)]phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(1S)-1-(Dimethylaminoethyl)]phenol(139306-10-8)
• EPA Substance Registry System: 3-[(1S)-1-(Dimethylaminoethyl)]phenol(139306-10-8)

Safety Data

• Statements: 36-43
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 139306-10-8(Hazardous Substances Data)

Usage

Description

NAP 226-90 is a metabolite of rivastigmine that is formed by hydrolysis.

Chemical Properties

off-white to pale yellow crysta

Uses

Different sources of media describe the Uses of 139306-10-8 differently. You can refer to the following data:
1. S-Enantiomer metabolite of Rivastigmine, a brain selective acetylcholinesterase inhibitor
2. NAP 226-90 (Rivastigmine EP Impurity A; Rivastigmin USP Related Compound C) is a S-Enantiomer metabolite of Rivastigmine, a brain selective acetylcholinesterase inhibitor.

InChI:InChI=1/C10H15NO/c1-8(11(2)3)9-5-4-6-10(12)7-9/h4-8,12H,1-3H3/t8-/m0/s1

Upstream product

• 105601-04-5 (+/-)-3-<1-(Dimethylamino)ethyl>phenol 
• 50-00-0 formaldehyd 
• 173098-21-0 1-Ethenyl-3-(phenylmethoxy)benzene 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 23308-82-9 (R)-(+)-1-(3-methoxyphenyl)-1-ethanol 
• 89691-63-4 1-(3-methoxy)-phenylethanol 
• 218900-56-2 (S)-[1-(3-methoxyphenyl)ethyl]carbamic acid tert-butyl ester 
• 121-71-1 3-Hydroxyacetophenone 
• 124-40-3 dimethyl amine 
• 118761-92-5 N-methyl-[1-(3'-methoxylphenyl)ethylidene]amine 
• 1233378-72-7 [3-[(1R)-1-methylsulfonyloxyethyl]phenyl] methanesulfonate 
• 1017234-21-7 3-((S)-1-((S)-1-phenylethylamino)ethyl)phenol 
• 894079-42-6 3-[(S)-1-(methylamino)ethyl]phenol 

Downstream Products

• 123441-03-2 rivastigmine tartrate 
• 851086-92-5 S-rivastigmine-d-amphetamine 
• 1104546-31-7 S-rivastigmine-d-methamphetamine 
• 851086-86-7 S-rivastigmine-l-amphetamine 
• 851086-85-6 3-((S)-1-(dimethylamino)ethyl)phenyl methyl-((R)-1-phenylpropan-2 yl)carbamate 
• 123441-03-2 rivastigmin 
• 851086-87-8 S-rivastigmine-desmethylselegiline 
• 851086-83-4 C₂₀H₂₆N₂O₂ 
• 851086-84-5 S-rivastigmine-atomoxetine 
• 851086-91-4 C₁₉H₂₄N₂O₂ 
• 1046270-29-4 S-rivastigmine-fluoxetine 
• 1046270-42-1 C₂₀H₃₀N₂O₄ 
• 1046270-43-2 C₂HF₃O₂*C₂₀H₃₀N₂O₄ 
• 1016225-06-1 C₁₇H₁₈N₂O₅ 

Relevant articles and documents

Purification method of carafine intermediate

To 3 - hydroxyacetophenone as a raw material, the intermediate 3 - [1 - (dimethylamino) ethyl] phenol is formed by reaction with dimethylamine, and the intermediate is subjected to resolution and purification by a specific resolution system to obtain S - 3 - [1 - (dimethylamino) ethyl] phenol. Compared with the preparation method of the intermediate prepared by the method, the preparation method has the advantages of low cost, high yield, good effect, less environmental pollution, reduced residue of inorganic salt, and favorability for large-scale industrial production.

SYNTHESIS OF NOVEL INTERMEDIATE(S) FOR PREPARING RIVASTIGMINE

The present invention relates to novel intermediate(s), which are useful for the preparation of Rivastigmine compound of formula (I) and its pharmaceutically acceptable salts. The present invention further relates to the processes for the preparation of such novel intermediate(s) and preparation of Rivastigmine using such novel intermediate(s).

Group-assisted Purification (GAP) Chemistry/Technology in synthesizing the chiral intermediate of rivastigmine and its ?-Alkyl benzylamine analogues

Introduction of (S)-configuration is the key step in the synthesis of the anti-dementia drug Rivastigmine. Twenty-one alkylation products were obtained through simple washing with hexane/ethyl acetate (v/v: 10/1) in good yields (>85%) and high diastereoselectivity (up to >99:1 dr). Moreover, the chiral auxiliary could be easily dissociated and readily regenerated. That is, the synthesis was proved to follow group-assisted purification (GAP) chemistry/technology. In addition, the chiral amine produced by this asymmetric alkylation reaction was effectively used in the synthesis of Rivastigmine.