Aceclidine

Base Information

• Chemical Name: Aceclidine
• CAS No.: 827-61-2
• Deprecated CAS: 72353-53-8
• Molecular Formula: C₉H₁₅NO₂
• Molecular Weight: 169.224
• Hs Code.: 2933990090
• European Community (EC) Number: 212-574-1
• NSC Number: 758239,657843
• UNII: 0578K3ELIO
• DSSTox Substance ID: DTXSID2045658
• Nikkaji Number: J48.379F
• Wikipedia: Aceclidine
• Wikidata: Q2362603
• NCI Thesaurus Code: C81044
• Metabolomics Workbench ID: 71447
• ChEMBL ID: CHEMBL20835
• Mol file: 827-61-2.mol

Synonyms:aceclidin;aceclidine;aceclidine hydrochloride;Glaucadrine;Glaucocare;Glaucostat;Glaucotat

Chemical Property of Aceclidine

Chemical Property:

• Vapor Pressure: 0.107mmHg at 25°C
• Refractive Index: 1.4780 (estimate)
• Boiling Point: 221.5 °C at 760 mmHg
• PKA: 9.22±0.33(Predicted)
• Flash Point: 85 °C
• PSA: 29.54000
• Density: 1.0873 (rough estimate)
• LogP: 0.58160
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 169.110278721
• Heavy Atom Count: 12
• Complexity: 185

Purity/Quality:

98%,99%, ^*data from raw suppliers

Aceclidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CN2CCC1CC2
• Recent ClinicalTrials: Phase 3 Efficacy Study of LNZ101 for the Treatment of Presbyopia
• Therapeutic Function: Miotic, Cholinomimetic

Technology Process of Aceclidine

There total 7 articles about Aceclidine 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: 90.0%

acetic anhydride (108-24-7) + 3-quinuclidinol (1619-34-7) → 3-acetoxyquinuclidine (827-61-2,59653-40-6,59653-42-8,72353-53-8)

Guidance literature:

for 4h; Heating;

DOI:10.1080/00397919208021320

Reference yield:

3-quinuclidinol (1619-34-7) → 3-acetoxyquinuclidine (827-61-2,59653-40-6,59653-42-8,72353-53-8)

Guidance literature:

With acetic anhydride; In pyridine; water;

Reference yield:

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-acetoxyquinuclidine (827-61-2,59653-40-6,59653-42-8,72353-53-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere

2.1: Reflux

2.2: 20 °C

3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C

3.2: 1.5 h

4.1: 2 h / 20 °C

With potassium tert-butylate; water; sodium hydroxide; In toluene; 1.1: |Dieckmann Condensation;

upstream raw materials:

acetic anhydride

3-quinuclidinol

3-Acetoxy-1-(2-methyl-acryloyloxymethyl)-1-azonia-bicyclo[2.2.2]octane; chloride

3-quinuclidinone hydrochloride

Downstream raw materials:

p-methylbenzoyloxymethyl-3-acetoxyquinuclidinium chloride

p-chlorobenzoyloxymethyl-3-acetoxyquinuclidinium chloride

m-nitrobenzoyloxymethyl-3-acetoxyquinuclidinium chloride

1-(phenylacetoxy)-3-acetoxyquinuclidinium chloride

Refernces

• 1、 -. "PHARMACEUTICAL COMPOSITION FOR USE IN MEDICAL AND VETERINARY OPHTHALMOLOGY". . . Retrieved 2012/05/04.
• 2、 Han, Xiang-Yu,Liu, He,Liu, Chun-He,Wu, Bo,Chen, Lan-Fu,Zhong, Bo-Hua,Liu, Ke-Liang. "Synthesis of the optical isomers of a new anticholinergic drug, penehyclidine hydrochloride (8018)". . p. 1979 - 1982. Retrieved 2007/10/03.