1-Azoniabicyclo[2.2.2]octan-3-one;chloride

Base Information

• Chemical Name: 1-Azoniabicyclo[2.2.2]octan-3-one;chloride
• CAS No.: 1193-65-3
• Molecular Formula: C7H12ClNO
• Molecular Weight: 161.631
• Hs Code.: 29333990
• Mol file: 1193-65-3.mol

Synonyms:

Chemical Property of 1-Azoniabicyclo[2.2.2]octan-3-one;chloride

Chemical Property:

• Appearance/Colour: white or yelloish powder
• Vapor Pressure: 0.257mmHg at 25°C
• Melting Point: >300 ºC (dec.)
• Boiling Point: 204.9ºCat 760 mmHg
• Flash Point: 78.1ºC
• PSA: 20.31000
• LogP: 1.02100
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: 0.1 g/mL, clear
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 161.0607417
• Heavy Atom Count: 10
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

3-Quinuclidinone HCl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C[NH+]2CCC1C(=O)C2.[Cl-]
• Uses: 3-Quinuclidinone Hydrochloride is used in the synthesis of cevimeline, a thiolating agent. Also used in the preparation of novel CB1 and CB2 cannabinoid receptor ligands.

Technology Process of 1-Azoniabicyclo[2.2.2]octan-3-one;chloride

There total 8 articles about 1-Azoniabicyclo[2.2.2]octan-3-one;chloride 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: 82.0%

3-quinuclidinol (1619-34-7) → 3-quinuclidinone hydrochloride (1193-65-3)

Guidance literature:

3-quinuclidinol; With 1-methyl-1H-imidazole; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen; In acetonitrile; at 70 ℃; for 1.5h;

With hydrogenchloride; In diethyl ether; acetonitrile; for 0.5h;

DOI:10.1021/ja409241h

Reference yield: 80.0%

ethyl 1-(2-methoxy-2-oxoethyl) piperidine-4-carboxylate (71172-59-3) → 3-quinuclidinone hydrochloride (1193-65-3)

Guidance literature:

ethyl 1-(2-methoxy-2-oxoethyl) piperidine-4-carboxylate; With potassium tert-butylate; In toluene; at 111 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In water; for 14h; Reflux;

With potassium carbonate; In water; Solvent; Reagent/catalyst;

DOI:10.2174/1570178612666150113231048

Reference yield: 79.0%

(S)-quinuclidin-3-ol (3684-26-2,25333-42-0,34583-34-1,1619-34-7) → 3-quinuclidinone hydrochloride (1193-65-3)

Guidance literature:

(S)-quinuclidin-3-ol; With dimethylsulfide; triethylamine; In chloroform; at -15 - -10 ℃; Inert atmosphere;

With N-chloro-succinimide; In chloroform; at -15 - -10 ℃; for 4h; Inert atmosphere;

upstream raw materials:

2-Ethoxycarbonyl-3-oxoquinuclidine oxime hydrochloride

1-ethoxycarbonylmethyl-piperidine-4-carboxylic acid methyl ester

toluene

(S)-quinuclidin-3-ol

Downstream raw materials:

cis-2-(2'-Hydroxybenzylidene)-3-oxoquinuclidine

piperidin-1-yl-acetonitrile

1,3-diaza-bicyclo[3.2.2]nonan-4-one

cis-2-(diphenylmethyl)-N-(phenylmethyl)-1-azabicyclo<2.2.2>octan-3-amine

Refernces

• 1、 Soni, Jigar Y.,Premasagar,Thakore, Sonal. "An improved and simple route for the synthesis of 3-quinuclidinone hydrochloride". . p. 277 - 279. Retrieved 2015/06/22.
• 2、 Steves, Janelle E.,Stahl, Shannon S.. "Copper(I)/ABNO-catalyzed aerobic alcohol oxidation: Alleviating steric and electronic constraints of Cu/TEMPO catalyst systems". supporting information. p. 15742 - 15745. Retrieved 2013/11/06.