1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride

Base Information

• Chemical Name: 1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride
• CAS No.: 52601-23-7
• Molecular Formula: C8H13NO2.ClH
• Molecular Weight: 191.658
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30480917
• Mol file: 52601-23-7.mol

Synonyms:52601-23-7;1-AZABICYCLO[2.2.2]OCTANE-2-CARBOXYLIC ACID HYDROCHLORIDE;2-Quinuclidinecarboxylic acid, hydrochloride;Quinuclidine-2-carboxylic acid hydrochloride;MFCD00168044;1-azabicyclo[2.2.2]octane-2-carboxylic acid;hydrochloride;1-Azabicyclo[2.2.2]octane-2-carboxylic acid, (Hydrochloride) (1:1);1-Azabicyclo[2.2.2]octane-2-carboxylic acid,hydrochloride;SCHEMBL5473763;DTXSID30480917;quinuclidine-2-carboxylic acid hcl;CS-B0592;AKOS037478282;AB87003;AB92114;AS-37994;SY245308;CS-0005671;(2r)-quinuclidine-2-carboxylic Acid Hydrochloride;1-Azabicyclo[2.2.2]octane-2-carboxylic acid HCl;1-AZABICYCLO[2.2.2]OCTANE-2-CARBOXYLICACIDHYDROCHLORIDE;1-Azabicyclo[2.2.2]octane-2-carboxylic acid--hydrogen chloride (1/1)

Chemical Property of 1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride

Chemical Property:

• Melting Point: 304-307℃ (DEC.)
• PSA: 40.54000
• LogP: 1.29520
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 191.0713064
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

99% ^*data from raw suppliers

Quinuclidine-2-carboxylicacidhydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CN2CCC1CC2C(=O)O.Cl

Technology Process of 1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride

There total 7 articles about 1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride 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:

quinuclidine-2-carbonitrile (90196-91-1,885517-05-5) → quinuiclidine-2-carboxylic acid hydrochloride (52601-23-7,94160-98-2,52730-01-5)

Guidance literature:

quinuclidine-2-carbonitrile; With hydrogenchloride; at 110 ℃; for 5h;

With sodium hydroxide; In water;

With hydrogenchloride; In water;

DOI:10.1021/acs.jmedchem.9b01427

Reference yield:

4-(2-Hydroxyethyl)piperidine (622-26-4) → quinuiclidine-2-carboxylic acid hydrochloride (52601-23-7,94160-98-2,52730-01-5)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydroxide / water; tert-butyl alcohol / 10 - 23 °C

2: pyridine-SO₃ complex; triethylamine / dimethyl sulfoxide / 1.5 h / 10 - 20 °C

3: hydrogenchloride / water; diethyl ether / 1.5 h / 0 - 10 °C

4: triethylamine / tetrahydrofuran / 2 h / 0 - 10 °C

5: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C

6: triethylamine / acetonitrile / Reflux

7: hydrogenchloride / 5 h / 110 °C

With hydrogenchloride; pyridine-SO₃ complex; triethylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol;

DOI:10.1021/acs.jmedchem.9b01427

Reference yield:

methanesulfonic acid 1-cyano-2-piperidin-4-yl-ethyl ester → quinuiclidine-2-carboxylic acid hydrochloride (52601-23-7,94160-98-2,52730-01-5)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / acetonitrile / Reflux

2: hydrogenchloride / 5 h / 110 °C

With hydrogenchloride; triethylamine; In acetonitrile;

DOI:10.1021/acs.jmedchem.9b01427

upstream raw materials:

4-(2-Hydroxyethyl)piperidine

4-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester

tert-butyl 4-(formylmethyl)piperidine-1-carboxylate

tert-butyl 4-(2-cyano-2-hydroxyethyl)piperidine-1-carboxylate

Refernces