(R)-Mequitazine

Base Information

• Chemical Name: (R)-Mequitazine
• CAS No.: 147780-50-5
• Molecular Formula: C₂₀H₂₂N₂S
• Molecular Weight: 322.474
• UNII: 05VP796JC6
• Nikkaji Number: J2.972.564K
• Wikidata: Q27236150
• Pharos Ligand ID: YRH3MZVZM1UD
• ChEMBL ID: CHEMBL1367006
• Mol file: 147780-50-5.mol

Synonyms:(R)-Mequitazine;147780-50-5;(+)-Mequitazine;Mequitazine, (R)-;(R)-(+)-Mequitazine;05VP796JC6;V-0162;UNII-05VP796JC6;J2.972.564K;10H-Phenothiazine, 10-((3R)-1-azabicyclo(2.2.2)oct-3-ylmethyl)-;10H-Phenothiazine, 10-(1-azabicyclo(2.2.2)oct-3-ylmethyl)-, (R)-;l-mequitazine;(R)-10-(quinuclidin-3-ylmethyl)-10H-phenothiazine;10H-Phenothiazine, 10-[(3R)-1-azabicyclo[2.2.2]oct-3-ylmethyl]-;10-(((3R)-1-Azabicyclo(2.2.2)octane-3alpha-yl)methyl)-10H-phenothiazine;vo162;NCIStruc1_001806;NCIStruc2_001597;SCHEMBL18208;CHEMBL1367006;10-[[(3R)-1-azabicyclo[2.2.2]octan-3-yl]methyl]phenothiazine;NCGC00014679;NCI303612;AKOS015963224;NCGC00014679-02;NCGC00097782-01;PD132506;Q27236150;10-(((3R)-1-AZABICYCLO(2.2.2)OCTANE-3.ALPHA.-YL)METHYL)-10H-PHENOTHIAZINE

Chemical Property of (R)-Mequitazine

Chemical Property:

• Vapor Pressure: 5.51E-09mmHg at 25°C
• Melting Point: 130-131°C
• Refractive Index: 1.707
• Boiling Point: 469.4°C at 760 mmHg
• Flash Point: 237.7°C
• PSA: 31.78000
• Density: 1.28g/cm³
• LogP: 4.63400
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 322.15036988
• Heavy Atom Count: 23
• Complexity: 398

Purity/Quality:

97% ^*data from raw suppliers

(R)-(+)-Mequitazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CCC1C(C2)CN3C4=CC=CC=C4SC5=CC=CC=C53
• Isomeric SMILES: C1CN2CCC1[C@H](C2)CN3C4=CC=CC=C4SC5=CC=CC=C53
• Uses: R-Enantiomer of Mequitazine. It is an antihistamine

Technology Process of (R)-Mequitazine

There total 11 articles about (R)-Mequitazine 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: 72.0%

10H-phenothiazine (92-84-2) + (3R)-1-azabicyclo[2.2.2]octan-3-ylmethyl methanesulfonate hydrochloride → (+)-R-mequitazine (147780-50-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; for 2.5h; Inert atmosphere; Reflux;

DOI:10.1021/ol2012567

Reference yield:

C20H20N2S*ClH (1632121-46-0) → (+)-R-mequitazine (147780-50-5) + (-)-Mequitazine

Guidance literature:

With [Ir(COD)₂]SbF₆; hydrogen; iodine; O,O'-(1,1'-biphenyl-2,2'-diyl)-N,N'-bis[(S,S)-1-phenyl-ethyl]phosphoramidite; In tetrahydrofuran; at 50 ℃; for 48h; under 67506.8 Torr; Overall yield = 85 %; enantioselective reaction; Autoclave;

DOI:10.1055/s-0033-1341274

Reference yield:

tert-butyl 2-[(3R,4S)-3-ethenylpiperidin-4-yl]acetate (52346-11-9) → (+)-R-mequitazine (147780-50-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

2.1: thionyl chloride / dichloromethane / 2 h / 0 °C / Inert atmosphere; Reflux

3.1: potassium carbonate; sodium iodide / acetonitrile / 2 h / Inert atmosphere; Reflux

4.1: trifluoroacetic acid / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

4.3: -78 - 20 °C

5.1: pyridine / chloroform / Inert atmosphere

6.1: potassium tert-butylate / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 2.5 h / Inert atmosphere; Reflux

With pyridine; lithium aluminium tetrahydride; thionyl chloride; potassium tert-butylate; potassium carbonate; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/ol2012567

upstream raw materials:

tert-butyl 2-[(3R,4S)-3-ethenylpiperidin-4-yl]acetate

(3R,4S)-4-(2-chloroethyl)-3-ethenylpiperidine

(3R)-3-ethenyl-1-azabicyclo[2.2.2]octane

(3R)-1-azabicyclo[2.2.2]octan-3-ylmethanol

Refernces

• 1、 -. "VINYL QUINUCLIDINE USEFUL AS A SYNTHESIS INTERMEDIATE IN THE PREPARATION OF (R)-MEQUITAZINE". . . Retrieved 2013/11/19.