Exelon

Base Information

• Chemical Name: Exelon
• CAS No.: 105601-20-5
• Molecular Formula: C14H22N2O2
• Molecular Weight: 250.341
• Hs Code.: 2924299090
• European Community (EC) Number: 691-247-9
• DSSTox Substance ID: DTXSID70274453,DTXSID40861278
• Nikkaji Number: J425.951C
• ChEMBL ID: CHEMBL151763
• Mol file: 105601-20-5.mol

Synonyms:(S)-N-ethyl-3-((1-dimethyl-amino)ethyl)-N-methylphenylcarbamate;713, ENA;713, SDZ ENA;ENA 713;ENA 713, SDZ;ENA-713;ENA713;Exelon;Hydrogen Tartrate, Rivastigmine;rivastigmine;Rivastigmine Hydrogen Tartrate;RivastigmineTartrate;SDZ ENA 713;Tartrate, Rivastigmine Hydrogen

Chemical Property of Exelon

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
• 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

(±)-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
• Recent ClinicalTrials: Cognitive Decline in Non-demented PD
• Recent EU Clinical Trials: A randomised, double blind, placebo controlled trial to evaluate the effect of Rivastigmine on gait in people with Parkinson’s disease who have fallen.
• Uses: (±)-Rivastigmine is a brain selective acetylcholinesterase inhibitor. Nootropic.

Technology Process of Exelon

There total 13 articles about Exelon 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: 71.2%

3-(1-bromoethyl)phenyl ethyl(methyl)carbamate (1392101-39-1) + dimethyl amine (124-40-3) → rac-rivastigmine (105601-20-5,415973-05-6)

Guidance literature:

3-(1-bromoethyl)phenyl ethyl(methyl)carbamate; dimethyl amine; In methanol; at 26 - 28 ℃; for 16 - 20h;

With hydrogenchloride; In water; at 12 - 15 ℃;

With sodium carbonate; In water; at 15 - 20 ℃; pH=2 - 11; Product distribution / selectivity;

Reference yield: 66.0%

N-ethyl-N-methylcarbamoyl chloride (42252-34-6) + (+/-)-3-<1-(Dimethylamino)ethyl>phenol (105601-04-5) → rac-rivastigmine (105601-20-5,415973-05-6)

Guidance literature:

With potassium carbonate; In acetonitrile; at 70 - 80 ℃;

Reference yield: 55.4%

1-(N-ethyl-N-methylaminocarbonyloxy)-3-acetylbenzene (855300-09-3) + dimethyl amine (124-40-3) → rac-rivastigmine (105601-20-5,415973-05-6)

Guidance literature:

dimethyl amine; With hydrogenchloride; In methanol; water; at 5 - 8 ℃; for 0.5h;

1-(N-ethyl-N-methylaminocarbonyloxy)-3-acetylbenzene; With sodium cyanoborohydride; In methanol; water; at 8 - 26 ℃; for 48h;

With hydrogenchloride; sodium carbonate; more than 3 stages; Product distribution / selectivity;

upstream raw materials:

N-ethyl-N-methylcarbamoyl chloride

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

C₁₇H₁₈N₂O₅

N-Ethylmethylamine

Downstream raw materials:

(R)-3-(1-(dimethylamino)ethyl) phenylethyl(methyl)carbamate

rivastigmin

R-rivastigmine (-) DPTTA salt

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

Refernces

• 1、 -. "Amorphous and crystalline forms of rivastigmine hydrogentartrate". Page/Page column 11. . Retrieved 2008/12/06.
• 2、 -. "Process for the preparation of phenylcarbamates". Page/Page column 3. . Retrieved 2010/11/28.