(R)-Rivastigmine

Base Information

• Chemical Name: (R)-Rivastigmine
• CAS No.: 415973-05-6
• Molecular Formula: C14H22N2O2
• Molecular Weight: 250.33700
• Hs Code.: 2924299090
• UNII: Z25UDQ15MV
• DSSTox Substance ID: DTXSID90194422
• Nikkaji Number: J2.138.266C
• Wikidata: Q27294895
• Mol file: 415973-05-6.mol

Synonyms:(R)-Rivastigmine;415973-05-6;Rivastigmine, (R)-;(R)-3-(1-(Dimethylamino)ethyl)phenyl ethyl(methyl)carbamate;SDZ-212712;Z25UDQ15MV;[3-[(1R)-1-(dimethylamino)ethyl]phenyl] N-ethyl-N-methylcarbamate;Carbamic acid, N-ethyl-N-methyl-, 3-((1R)-1-(dimethylamino)ethyl)phenyl ester;3-[(1R)-1-(DIMETHYLAMINO)ETHYL]PHENYL N-ETHYL-N-METHYLCARBAMATE;UNII-Z25UDQ15MV;RIVASTIGMINE TARTRATE R-ISOMER;Rivastigmine specified impurity D [EP];Rivastigmine hydrogen tartrate specified impurity D [EP];SCHEMBL13841811;DTXSID90194422;RIVASTIGMINE IMPURITY D [EP IMPURITY];RIVASTIGMINE TARTRATE R-ISOMER [USP-RS];EN300-18983660;J-502343;Q27294895;(R)-3-(1-(Dimethylamino)ethyl)phenylethyl(methyl)carbamate;RIVASTIGMINE HYDROGEN TARTRATE IMPURITY D [EP IMPURITY];(S)-1-(3-((ethyl(methyl)carbamoyl)oxy)phenyl)-N,N-dimethylethanamine

Chemical Property of (R)-Rivastigmine

Chemical Property:

• Boiling Point: 316.2±34.0 °C(Predicted)
• PKA: 8.62±0.50(Predicted)
• PSA: 32.78000
• Density: 1.038±0.06 g/cm3(Predicted)
• LogP: 2.75970
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 250.168127949
• Heavy Atom Count: 18
• Complexity: 269

Purity/Quality:

99% ^*data from raw suppliers

(R)-Rivastigmine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(C)C(=O)OC1=CC=CC(=C1)C(C)N(C)C
• Isomeric SMILES: CCN(C)C(=O)OC1=CC=CC(=C1)[C@@H](C)N(C)C

Technology Process of (R)-Rivastigmine

There total 86 articles about (R)-Rivastigmine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (S)-3-(1-aminoethyl)phenyl ethyl(methyl)carbamate (1176026-49-5) → rivastigmin (123441-03-2,415973-05-6)

Guidance literature:

With sodium tris(acetoxy)borohydride; In dichloromethane; water; at 20 ℃; for 16.5h;

DOI:10.1016/j.tet.2012.06.031

Reference yield: 98.0%

N-ethyl-N-methylcarbamoyl chloride (42252-34-6) + (S)-3-(1-dimethylaminoethyl)phenol (139306-10-8) → rivastigmin (123441-03-2,415973-05-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 5h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201504052

Reference yield: 97.6%

N-ethyl-N-methylcarbamoyl chloride (42252-34-6) + (+/-)-3-<1-(Dimethylamino)ethyl>phenol (105601-04-5) → rivastigmin (123441-03-2,415973-05-6)

Guidance literature:

With sodium carbonate; In acetone; for 8h; Solvent;

upstream raw materials:

N-ethyl-N-methylcarbamoyl chloride

(+/-)-3-<1-(Dimethylamino)ethyl>phenol

C₁₇H₁₈N₂O₅

N-Ethylmethylamine

Downstream raw materials:

(S)-N-ethyl-3-[(1-dimethylamino)ethyl]-N-methylphenylcarbamate di-p-toluoyl-D-tartrate

3-(1-methoxyethyl)phenyl N-ethyl-N-methylcarbamate

3-vinylphenyl N-ethyl-N-methylcarbamate

3-ethylphenyl N-ethyl-N-methylcarbamate