1,2-Diazabicyclo[2.2.2]octan-3-one

Base Information

• Chemical Name: 1,2-Diazabicyclo[2.2.2]octan-3-one
• CAS No.: 1632-26-4
• Molecular Formula: C6H10 N2 O
• Molecular Weight: 126.158
• DSSTox Substance ID: DTXSID60167527
• Nikkaji Number: J144.997D
• Wikidata: Q83036919
• Mol file: 1632-26-4.mol

Synonyms:1,2-DIAZABICYCLO(2.2.2)OCTAN-3-ONE;2-Azaquinuclidone-3;3-Oxo-1,2-diazabicyclo<2.2.2>octan;1,2-Diaza-3-oxobicyclo[2.2.2]octane;3-Keto-1,2-diazabicyclo<2.2.2>octan;

Chemical Property of 1,2-Diazabicyclo[2.2.2]octan-3-one

Chemical Property:

• PSA: 35.83000
• Density: 1.23g/cm³
• LogP: -0.04300
• Storage Temp.: -20°C Freezer
• Solubility.: Dichloromethane; Chloroform
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 126.079312947
• Heavy Atom Count: 9
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

1,2-Diazabicyclo[2.2.2]octan-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CCC1C(=O)N2
• Uses: 1,2-Diazabicyclo[2.2.2]octan-3-one is an intermediate used in the synthesis of Bicyclo Risperidone (B382800), which is an impurity of Risperidone (R525000); a combined serotonin (5-HT2) and dopamine (D2) receptor antagonist.

Technology Process of 1,2-Diazabicyclo[2.2.2]octan-3-one

There total 5 articles about 1,2-Diazabicyclo[2.2.2]octan-3-one 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: 100.0%

2-chloro-1,2-diazabicyclo(2.2.2)octan-3-one (97812-34-5) → dimethylchloroamine (1585-74-6) + 1,2-Diaza-3-oxobicyclo<2.2.2>octane (1632-26-4)

Guidance literature:

With dimethyl amine; at -5 - 0 ℃; for 0.5h; Product distribution;

DOI:10.1016/S0040-4020(01)96503-2

Reference yield:

1-Nitroso-4-(carbomethoxy)piperidine (13458-55-4) → 1,2-Diaza-3-oxobicyclo<2.2.2>octane (1632-26-4)

Guidance literature:

With hydrogen; iron(II) sulfate; palladium on activated charcoal; Yield given. Multistep reaction; 1) 50percent aq. ethanol, 18 h, 2a) heating in tetralin, 2b) 12 h, room temperature;

DOI:10.1021/jo01307a024

Reference yield:

pyridine-4-carboxylic acid (55-22-1) → 1,2-Diaza-3-oxobicyclo<2.2.2>octane (1632-26-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / conc. H₂SO₄ / 24 h / Heating

2: 1) H₂, 2) 8 N NaNO₂, acetic acid / 1)PtO₂ / 1) acetic acid, 5 - 40 psi, 2) 48 h, water - actic acid

3: 1) H₂, ferrous sulfate / 1) 10percent Pd/C / 1) 50percent aq. ethanol, 18 h, 2a) heating in tetralin, 2b) 12 h, room temperature

With sulfuric acid; hydrogen; iron(II) sulfate; acetic acid; sodium nitrite; platinum(IV) oxide; palladium on activated charcoal;

DOI:10.1021/jo01307a024

upstream raw materials:

1-Nitroso-4-(carbomethoxy)piperidine

2-chloro-1,2-diazabicyclo(2.2.2)octan-3-one

pyridine-4-carboxylic acid

4-pyridinecarboxylic acid, methyl ester

Refernces

• 1、 Shustov, G. V.,Tavakalyan, N. B.,Kostyanovsky, R. G.. "ASYMMETRICAL NITROGEN-40; GEMINAL SYSTEM-26. N-CHLOROHYDRAZINES". . p. 575 - 584. Retrieved 2007/10/02.