Etafedrine

Base Information

• Chemical Name: Etafedrine
• CAS No.: 48141-64-6
• Molecular Formula: C12H19 N O
• Molecular Weight: 193.289
• European Community (EC) Number: 256-359-0,231-677-2
• UNII: 2Y6VQU63E8
• DSSTox Substance ID: DTXSID201016521
• Nikkaji Number: J319.973H
• Wikipedia: Etafedrine
• Wikidata: Q5402378
• NCI Thesaurus Code: C76539
• Metabolomics Workbench ID: 152731
• Mol file: 48141-64-6.mol

Synonyms:etafedrine;etafedrine hydrochloride;etafedrine hydrochloride, (R-(R*,S*))-isomer;etafedrine, (R*,S*)-isomer;etafedrine, R-(R*,S*);etaphedrine;L-N-ethylephedrine

Chemical Property of Etafedrine

Chemical Property:

• Boiling Point: 294.8°Cat760mmHg
• Flash Point: 104.5°C
• PSA: 23.47000
• Density: 0.995g/cm³
• LogP: 2.06020
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 193.146664230
• Heavy Atom Count: 14
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Etafedrine

There total 9 articles about Etafedrine 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: 96.0%

(4S,5R)-2,3,4-Trimethyl-5-phenyl-oxazolidine (258827-42-8) → (1R,2S)-1-phenyl-2-(ethylmethylamino)propanol (48141-64-6)

Guidance literature:

With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile;

Reference yield: 95.0%

ephedrine (299-42-3,7009-81-6,90-83-5,6912-63-6) + acetonitrile (75-05-8,26809-02-9) → (1R,2S)-1-phenyl-2-(ethylmethylamino)propanol (48141-64-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 24h; Ambient temperature;

DOI:10.1016/S0040-4039(97)01728-0

Reference yield: 75.0%

(1R,2S)-N-<(2-Hydroxy-2-phenyl)-1-methyl-ethyl>-N-methylacetamid (2272-83-5) → (1R,2S)-1-phenyl-2-(ethylmethylamino)propanol (48141-64-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 55 ℃; for 2h;

DOI:10.1007/BF00811546

upstream raw materials:

diethyl sulfate

ephedrine

ethyl bromide

(1R,2S)-N-<(2-Hydroxy-2-phenyl)-1-methyl-ethyl>-N-methylacetamid

Downstream raw materials:

(1R,2S)-α-<1-(ethylmethylamino)ethyl>-N-cyclohexylbenzylamine

2-[(1R,2S)-2-(Ethyl-methyl-amino)-1-phenyl-propyl]-isoindole-1,3-dione

(2S)-1<2-(2-Dimethylaminoethyl)phenyl>-N-ethyl-N-methyl-2-propanamin

(1R,2S)-α-<1-(ethylmethylamino)ethyl>benzylamine

Refernces

• 1、 Ruppenthal, Simon,Brückner, Reinhard. "Asymmetric Sulfinylations of N-Methylephedrine-Modified Tri- or Tetraalkyl Zincates by Symmetric Diaryl Sulfoxides". supporting information. p. 2518 - 2530. Retrieved 2018/06/11.
• 2、 Henin, Francoise,Letinois, Stephane,Muzart, Jacques. "Nitriles under palladium-catalyzed hydrogenation conditions as substitutes for aldehydes in the reaction with 1,2-amino alcohols: Formation of 1,3-oxazolidines and reductive N-alkylation". . p. 7187 - 7190. Retrieved 2007/10/03.