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C1CN2CCC1(CC2)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1-azabicyclo[2.2.2]octan-4-ol |
|---|---|
| IUPAC Name | — |
| CAS Number | 26458-74-2 |
| Database ID | 141290 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1-azabicyclo[2.2.2]octan-4-ol (CAS 26458-74-2) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 141290
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-85d0ea088e034468b5cfef55442bcef7Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5eb5eeceb00146febae2a6c092899adfConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Oxalyl chloride (1.5 ml, 0.017 mol) was added to a solution of oxothien-2-yl-acetic acid (2.24 g, 0,014 mol) and dimethylformamide (one drop) in 30 ml of chloroform (etanol free) at 01C. The mixture was stirred and allowed to warm at room temperature. After one hour the solvent was evaporated. The residue was dissolved in chloroform and evaporated again. This procedure was repeated two times. The product obtained was disolved in CHCl3 (30 ml) and added to a suspension of 1.1 g (0.009 mols) of 4-hydroxy-1-azabicyclo[2.2.2]octane, 1.8 ml of triethylamine (0,013 mols), 0.6 g (0.9 mmols) of N-(methylpolystyrene)-4-(methylamino) pyridine at 70° C. The mixture was refluxed for 1 hour, cooled, filtered and washed with water. The title product was extracted with a solution of diluted HCl, washed with CHCl3, basified with K2CO3 and extracted again with CHCl3. After removal of the solvent 1.47 g (45%) of a solid was obtained. 1H-NMR (dmso): δ 2.0 (m, 6H), 2.9 (m, 6H), 7.35 (m, 1H), 8.05 (m, 1H), 8.3 (m, 1H). After one hour the solvent was evaporated The residue was dissolved in chloroform evaporated again The product obtained The mixture was refluxed for 1 hour cooled filtered washed with water The title product was extracted with a solution of diluted HCl washed with CHCl3 extracted again with CHCl3 After removal of the solvent 1.47 g (45%) of a solid was obtained
Source ID: ord-1c46089016ad479db00a2611afd0a9ceConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Oxalyl chloride (1.5 ml, 0.017 mol) was added to a solution of oxothien-2-yl-acetic acid (2.24 g, 0.014 mol) and dimethylformamide (one drop) in 30 ml of chloroform (etanol free) at 0° C. The mixture was stirred and allowed to warm at room temperature. After one hour the solvent was evaporated. The residue was dissolved in chloroform and evaporated again. This procedure was repeated two times. The product obtained was disolved in CHCl3 (30 ml) and added to a suspension of 1.1 g (0.009 mols) of 4-hydroxy-1-azabicyclo[2.2.2]octane, 1.8 ml of triethylamine (0.013 mols), 0.6 g (0.9 mmols) of N-(methylpolystyrene)-4-(methylamino) pyridine at 70° C. The mixture was refluxed for 1 hour, cooled, filtered and washed with water. The title product was extracted with a solution of diluted HCl, washed with CHCl3, basified with K2CO3 and extracted again with CHCl3. After removal of the solvent 1.47 g (45%) of a solid was obtained. 1H-NMR (dorso): δ 2.0 (m, 6H), 2.9 (m, 6H), 7.35 (m, 1H), 8.05 (m, 1H), 8.3 (m, 1H). After one hour the solvent was evaporated The residue was dissolved in chloroform evaporated again The product obtained The mixture was refluxed for 1 hour cooled filtered washed with water The title product was extracted with a solution of diluted HCl washed with CHCl3 extracted again with CHCl3 After removal of the solvent 1.47 g (45%) of a solid was obtained
Source ID: ord-1eaa645a1184459f9f1f4156ba974bdaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Oxalyl chloride (1.5 ml, 0.017 mol) was added to a solution of oxothien-2-yl-acetic acid (2.24 g, 0.014 mol) and dimethylformamide (one drop) in 30 ml of chloroform (etanol free) at 01 C. The mixture was stirred and allowed to warm at room temperature. After one hour the solvent was evaporated. The residue was dissolved in chloroform and evaporated again. This procedure was repeated two times. The product obtained was disolved in CHCl3 (30 ml) and added to a suspension of 1.1 g (0.009 mols) of 4-hydroxy-1-azabicyclo[2.2.2]octane, 1.8 ml of triethylamine (0.013 mols), 0.6 g (0.9 mmols) of N-(methylpolystyrene)-4-(methylamino) pyridine at 70° C. The mixture was refluxed for 1 hour, cooled, filtered and washed with water. The title product was extracted with a solution of diluted HCl, washed with CHCl3, basified with K2CO3 and extracted again with CHCl3. After removal of the solvent 1.47 g (45%) of a solid was obtained. 1H-NMR (dmso): δ 2.0 (m, 6H), 2.9 (m, 6H), 7.35 (m, 1H), 8.05 (m, 1H), 8.3 (m, 1H). After one hour the solvent was evaporated The residue was dissolved in chloroform evaporated again The product obtained The mixture was refluxed for 1 hour cooled filtered washed with water The title product was extracted with a solution of diluted HCl washed with CHCl3 extracted again with CHCl3 After removal of the solvent 1.47 g (45%) of a solid was obtained
Source ID: ord-42883f8c369a4261b8cc25550abb472bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a vial containing 5-fluoro-1-(methylsulfonyl)-1H-indole-3-carboxylic acid (20 mg, 0.078 mmol; see Reference 10 for the synthesis) and trifluoroacetic anhydride (10.98 μl, 0.078 mmol) in toluene (259 μl) was added TFA (64.8 μl). After 30 min, quinuclidin-4-ol (8.24 mg, 0.065 mmol) was added and the mixture was stirred at RT overnight. Direct HPLC purification (after dilution with DMF and filtration) gave the title compound as a clear film. MS (ESI, pos. ion) m/z: 367.2 (M+1). Direct HPLC purification (after dilution with DMF and filtration)
Source ID: ord-b885b1d9b92d4236ac90212911fe267cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Oxalyl chloride (1.5 ml, 0.017 mol) was added to a solution of oxothien-2-yl-acetic acid (2.24 g, 0.014 mol) and dimethylformamide (one drop) in 30 ml of chloroform (ethanol free) at 01 C. The mixture was stirred and allowed to warm at room temperature. After one hour the solvent was evaporated. The residue was dissolved in chloroform and evaporated again. This procedure was repeated two times. The product obtained was dissolved in CHCl3 (30 ml) and added to a suspension of 1.1 g (0.009 mols) of 4-hydroxy-1-azabicyclo[2.2.2]octane, 1.8 ml of triethylamine (0.013 mols), 0.6 g (0.9 mmols) of N-(methylpolystyrene)-4-(methylamino)pyridine at 70° C. The mixture was refluxed for 1 hour, cooled, filtered and washed with water. The title product was extracted with a solution of diluted HCl, washed with CHCl3, basified with K2CO3 and extracted again with CHCl3. After removal of the solvent 1.47 g (45%) of a solid was obtained. 1H-NMR (dmso): δ 2.0 (m, 6H), 2.9 (m, 6H), 7.35 (m, 1H), 8.05 (m, 1H), 8.3 (m, 1H). After one hour the solvent was evaporated The residue was dissolved in chloroform evaporated again The product obtained The mixture was refluxed for 1 hour cooled filtered washed with water The title product was extracted with a solution of diluted HCl washed with CHCl3 extracted again with CHCl3 After removal of the solvent 1.47 g (45%) of a solid was obtained
Source ID: ord-70531b3bb2e848978820cf133dfeb449Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Oxalyl chloride (1.5 ml,0.017 mol) was added to a solution of oxothien-2-yl-acetic acid (2.24 g, 0,014 mol) and dimethylformamide (one drop) in 30 ml of chloroform (etanol free) at 0° C. The mixture was stirred and allowed to warm at room temperature. After one hour the solvent was evaporated. The residue was dissolved in chloroform and evaporated again. This procedure was repeated two times. The product obtained was disolved in CHCl3 (30 ml) and added to a suspension of 1.1 g (0,009 mols) of 4-hydroxy-1-azabicyclo[2.2.2]octane, 1.8 ml of triethylamine (0.013 mols), 0.6 g (0.9 mmols) of N-(methylpolystyrene)-4-(methylamino)pyridine at 70° C. The mixture was refluxed for 1 hour, cooled, filtered and washed with water. The title product was extracted with a solution of diluted HCl, washed with CHCl3, basified with K2CO3 and extracted again with CHCl3. After removal of the solvent 1.47 g (45%) of a solid was obtained. 1H-NMR (dmso): δ 2.0 (m, 6H), 2.9 (m,6H), 7.35 (m, 1H), 8.05 (m, 1H), 8.3 (m, 1H). After one hour the solvent was evaporated The residue was dissolved in chloroform evaporated again The product obtained The mixture was refluxed for 1 hour cooled filtered washed with water The title product was extracted with a solution of diluted HCl washed with CHCl3 extracted again with CHCl3 After removal of the solvent 1.47 g (45%) of a solid was obtained
Source ID: ord-2ca0a0ca7f354076abfd6ea8fe01a13eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Oxalyl chloride (1.5 ml, 0.017 mol) was added to a solution of oxothien-2-yl-acetic acid (2.24 g, 0,014 mol) and dimethylformamide (one drop) in 30 ml of chloroform (etanol free) at 01 C. The mixture was stirred and allowed to warm at room temperature. After one hour the solvent was evaporated. The residue was dissolved in chloroform and evaporated again. This procedure was repeated two times. The product obtained was disolved in CHCl3 (30 ml) and added to a suspension of 1.1 g (0,009 mols) of 4-hydroxy-1-azabicyclo[2.2.2]octane, 1.8 ml of triethylamine (0.013 mols), 0.6 g (0.9 mmols) of N-(methylpolystyrene)-4-(methylamino) pyridine at 70° C. The mixture was refluxed for 1 hour, cooled, filtered and washed with water. The title product was extracted with a solution of diluted HCl, washed with CHCl3, basified with K2CO3 and extracted again with CHCl3. After removal of the solvent 1.47 g (45%) of a solid was obtained. 1H-NMR (dmso): δ 2.0 (m, 6H), 2.9 (m, 6H), 7.35 (m, 1H), 8.05 (m, 1H), 8.3 (m, 1H). After one hour the solvent was evaporated The residue was dissolved in chloroform evaporated again The product obtained The mixture was refluxed for 1 hour cooled filtered washed with water The title product was extracted with a solution of diluted HCl washed with CHCl3 extracted again with CHCl3 After removal of the solvent 1.47 g (45%) of a solid was obtained
Source ID: ord-e294dee29056456b8f09d63d2fdd9dcaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Oxalyl chloride (1.5 ml, 0.017 mol) was added to a solution of oxothien-2-yl-acetic acid (2.24 g, 0,014 mol) and dimethylformamide (one drop) in 30 ml of chloroform (etanol free) at 01C. The mixture was stirred and allowed to warm at room temperature. After one hour the solvent was evaporated. The residue was dissolved in chloroform and evaporated again. This procedure was repeated two times. The product obtained was disolved in CHCl3 (30 ml) and added to a suspension of 1.1 g (0.009 mols) of 4-hydroxy-1-azabicyclo[2.2.2]octane, 1.8 ml of triethylamine (0,013 mols), 0.6 g (0.9 mmols) of N-(methylpolystyrene)-4-(methylamino) pyridine at 70° C. The mixture was refluxed for 1 hour, cooled, filtered and washed with water. The title product was extracted with a solution of diluted HCl, washed with CHCl3, basified with K2CO3 and extracted again with CHCl3. After removal of the solvent 1.47 g (45%) of a solid was obtained. 1H-NMR (dmso): δ 2.0 (m, 6H), 2.9 (m, 6H), 7.35 (m, 1H), 8.05 (m, 1H), 8.3 (m, 1H). After one hour the solvent was evaporated The residue was dissolved in chloroform evaporated again The product obtained The mixture was refluxed for 1 hour cooled filtered washed with water The title product was extracted with a solution of diluted HCl washed with CHCl3 extracted again with CHCl3 After removal of the solvent 1.47 g (45%) of a solid was obtained
Source ID: ord-1c46089016ad479db00a2611afd0a9ceConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-85d0ea088e034468b5cfef55442bcef7Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5eb5eeceb00146febae2a6c092899adfPubChem References
These sources are listed in the compound's public database record.
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