N-(1-azabicyclo(2.2.2)-oct-3-yl)-5-chlorospiro(benzofuran-2(3H),1'-cyclohexane)-7-carboxamide

Base Information

• Chemical Name: N-(1-azabicyclo(2.2.2)-oct-3-yl)-5-chlorospiro(benzofuran-2(3H),1'-cyclohexane)-7-carboxamide
• CAS No.: 138663-21-5
• Molecular Formula: C₂₁H₂₇ClN₂O₂
• Molecular Weight: 374.911
• DSSTox Substance ID: DTXSID50930181
• Nikkaji Number: J464.277E
• Wikidata: Q82905416
• ChEMBL ID: CHEMBL353196
• Mol file: 138663-21-5.mol

Synonyms:1-ACSFC;N-(1-azabicyclo(2.2.2)-oct-3-yl)-5-chlorospiro(benzofuran-2(3H),1'-cyclohexane)-7-carboxamide;N-(1-azabicyclo(2.2.2)-oct-3-yl)-5-chlorospiro(benzofuran-2(3H),1'-cyclohexane)-7-carboxamide, (+-)-isomer;N-(1-azabicyclo(2.2.2)-oct-3-yl)-5-chlorospiro(benzofuran-2(3H),1'-cyclohexane)-7-carboxamide, (R)-isomer

Chemical Property of N-(1-azabicyclo(2.2.2)-oct-3-yl)-5-chlorospiro(benzofuran-2(3H),1'-cyclohexane)-7-carboxamide

Chemical Property:

• Boiling Point: 500°Cat760mmHg
• Flash Point: 256.2°C
• PSA: 45.06000
• Density: 1.29g/cm³
• LogP: 4.31450
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 374.1761058
• Heavy Atom Count: 26
• Complexity: 542

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2(CC1)CC3=C(O2)C(=CC(=C3)Cl)C(=O)NC4CN5CCC4CC5
• Isomeric SMILES: C1CCC2(CC1)CC3=C(O2)C(=CC(=C3)Cl)C(=O)N[C@@H]4CN5CCC4CC5

Technology Process of N-(1-azabicyclo(2.2.2)-oct-3-yl)-5-chlorospiro(benzofuran-2(3H),1'-cyclohexane)-7-carboxamide

There total 8 articles about N-(1-azabicyclo(2.2.2)-oct-3-yl)-5-chlorospiro(benzofuran-2(3H),1'-cyclohexane)-7-carboxamide 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:

Spiro-(benzofuran-2(3H),1'-cyclohexan) (182-50-3) → N-(1-azabicyclo[2.2.2]oct-3(S)-yl)-5-chlorospiro(benzofuran-2(3H),1'-cyclohexane)-7-carboxamide (138663-21-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-butyllithium, tetramethylethylenediamine / 1.) hexane, RT, overnight, 2.) hexane, 1 h

2: 1.93 g / N-chlorosuccinimide / dimethylformamide / 48 h

3: thionyl chloride / CHCl₃ / 3 h / 40 °C

4: toluene / 2 h / Ambient temperature

With N-chloro-succinimide; n-butyllithium; thionyl chloride; N,N,N,N,-tetramethylethylenediamine; In chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00083a014

Reference yield:

2-(methoxymethoxy)benzaldehyde (5533-04-0) → N-(1-azabicyclo[2.2.2]oct-3(S)-yl)-5-chlorospiro(benzofuran-2(3H),1'-cyclohexane)-7-carboxamide (138663-21-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) methyllithium / 1.) THF, ether, 0 deg C, 2.) THF, ether, RT, 1.5 h

2: 23.5 g / acetic acid / H₂O / 78 h / Heating

3: 10.1 g / trifluoroacetic acid / 2 h / Heating

4: 1.) n-butyllithium, tetramethylethylenediamine / 1.) hexane, RT, overnight, 2.) hexane, 1 h

5: 1.93 g / N-chlorosuccinimide / dimethylformamide / 48 h

6: thionyl chloride / CHCl₃ / 3 h / 40 °C

7: toluene / 2 h / Ambient temperature

With N-chloro-succinimide; n-butyllithium; thionyl chloride; N,N,N,N,-tetramethylethylenediamine; methyllithium; acetic acid; trifluoroacetic acid; In chloroform; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00083a014

Reference yield:

salicylaldehyde (90-02-8) → N-(1-azabicyclo[2.2.2]oct-3(S)-yl)-5-chlorospiro(benzofuran-2(3H),1'-cyclohexane)-7-carboxamide (138663-21-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) potassium tert-butoxide, 2.) 18-crown-6-ether / 1.) acetonitrile, 15 deg C, 2.) acetonitrile, RT, 1 h

2: 1.) methyllithium / 1.) THF, ether, 0 deg C, 2.) THF, ether, RT, 1.5 h

3: 23.5 g / acetic acid / H₂O / 78 h / Heating

4: 10.1 g / trifluoroacetic acid / 2 h / Heating

5: 1.) n-butyllithium, tetramethylethylenediamine / 1.) hexane, RT, overnight, 2.) hexane, 1 h

6: 1.93 g / N-chlorosuccinimide / dimethylformamide / 48 h

7: thionyl chloride / CHCl₃ / 3 h / 40 °C

8: toluene / 2 h / Ambient temperature

With N-chloro-succinimide; n-butyllithium; thionyl chloride; 18-crown-6 ether; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; methyllithium; acetic acid; trifluoroacetic acid; In chloroform; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00083a014

upstream raw materials:

(S)-3-aminoquinuclidine

Spiro-(benzofuran-2(3H),1'-cyclohexan)

2-(methoxymethoxy)benzaldehyde

salicylaldehyde

Refernces