No renderable structure data available
C1CN(CCC1CC2=CC=CC=C2)CCNChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-(4-benzylpiperidin-1-yl)ethanamine |
|---|---|
| IUPAC Name | — |
| CAS Number | 25842-32-4 |
| Database ID | 2779831 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-(4-benzylpiperidin-1-yl)ethanamine (CAS 25842-32-4) 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 2779831
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-21320ae05f3347038a0a35600ddca3c5Conditions: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-(2-aminoethyl)-4-benzylpiperidine (13.0 g, 59.6 mmol), 1,8-diazabicyclo[5,4,0]-7-undecene (10.9 g, 71.7 mmol) and N,N-dimethylformamide (90.0 ml, 1.16 mol) was chilled to -30° C. To the mixture was added over 30 minutes a solution of (2S, 4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride (Reference Example, 18.0 g, 60.3 mmol) in N,N-dimethylformamide (90.0 ml, 1.16 mol) and the mixture was stirred for 15 hours at temperature of 15°-25° C. After distilling off the solvent, the reaction mixture was chromatographed on silica gel, eluted with CH2Cl2 /MeOH (9/1) and evaporated in vacuo to dryness to give the desired compound (14.3 g, 50.0%) as colorless amorphous substance. After distilling off the solvent the reaction mixture was chromatographed on silica gel eluted with CH2Cl2 /MeOH (9/1) evaporated in vacuo to dryness
Source ID: ord-c6d5e1d3fcb54a83a48220d146ac0044Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-21320ae05f3347038a0a35600ddca3c5Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-21320ae05f3347038a0a35600ddca3c5Conditions: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-(2-aminoethyl)-4-benzylpiperidine (13.0 g, 59.6 mmol), 1,8-diazabicyclo[5,4,0]-7-undecene (10.9 g, 71.7 mmol) and N,N-dimethylformamide (90.0 ml, 1.16 mol) was chilled to -30° C. To the mixture was added over 30 minutes a solution of (2S, 4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride (Reference Example, 18.0 g, 60.3 mmol) in N,N-dimethylformamide (90.0 ml, 1.16 mol) and the mixture was stirred for 15 hours at temperature of 15°-25° C. After distilling off the solvent, the reaction mixture was chromatographed on silica gel, eluted with CH2Cl2 /MeOH (9/1) and evaporated in vacuo to dryness to give the desired compound (14.3 g, 50.0%) as colorless amorphous substance. After distilling off the solvent the reaction mixture was chromatographed on silica gel eluted with CH2Cl2 /MeOH (9/1) evaporated in vacuo to dryness
Source ID: ord-c6d5e1d3fcb54a83a48220d146ac0044Conditions: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-(2-aminoethyl)-4-benzylpiperidine (13.0 g, 59.6 mmol), 1,8-diazabicyclo[5,4,0]-7-undecene (10.9 g, 71.7 mmol) and N,N-dimethylformamide (90.0 ml, 1.16 mol) was chilled to -30° C. To the mixture was added over 30 minutes a solution of (2S, 4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride (Reference Example, 18.0 g, 60.3 mmol) in N,N-dimethylformamide (90.0 ml, 1.16 mol) and the mixture was stirred for 15 hours at temperature of 15°-25° C. After distilling off the solvent, the reaction mixture was chromatographed on silica gel, eluted with CH2Cl2 /MeOH (9/1) and evaporated in vacuo to dryness to give the desired compound (14.3 g, 50.0%) as colorless amorphous substance. After distilling off the solvent the reaction mixture was chromatographed on silica gel eluted with CH2Cl2 /MeOH (9/1) evaporated in vacuo to dryness
Source ID: ord-c6d5e1d3fcb54a83a48220d146ac0044Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 2-(4-benzylpiperidino)-1-ethanamine (Example B1, 54.6 mg, 0.25 mmol), TEA (35 μL, 0.25 mmol) and 1,3-bis-(2,6-dimethyl-pyridin-4-yl)-urea (Example B1, 67.6 mg 0.25 mmol) in dioxane (2 mL) is heated at reflux for 24 h. The solvent is evaporated and the residue purified by HPLC to provide the title compound. is heated at reflux for 24 h The solvent is evaporated the residue purified by HPLC
Source ID: ord-e85a7bea8fe44e78ad591894a1e7ec73Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of CDI (178 mg, 1.1 mmol) in DMSO (5 mL) is added a solution of 2-(4-benzyl-piperidin-1-yl)-ethylamine (218 mg, 1 mmol) in DMSO (1 mL). The reaction mixture is stirred at 20° C. for 3 h. Methyl-(2-methyl-quinolin-4-yl)-amine (173 mg, 1 mmol) is added. To the resulting solution is added in a single portion NaHMDS (2 M in THF, 1.25 mL, 2.5 mmol). The reaction mixture is stirred at 20° C. for 24 h, then H2O (0.4 mL) is added. The reaction mixture is evaporated and the residue purified by preparative HPLC to provide the title compound. The reaction mixture is stirred at 20° C. for 24 h The reaction mixture is evaporated the residue purified by preparative HPLC
Source ID: ord-3925a18c660d4ba7bf8c3fa196ebf96eConditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of CDI (178 mg, 1.1 mmol) in DMSO (5 mL) is added a solution of 2-(4-benzyl-piperidin-1-yl)-ethylamine (218 mg, 1 mmol) in DMSO (1 mL). The reaction mixture is stirred at 20° C. for 3 h. Methyl-(2-methyl-quinolin-4-yl)-amine (173 mg, 1 mmol) is added. To the resulting solution is added in a single portion NaHMDS (2 M in THF, 1.25 mL, 2.5 mmol). The reaction mixture is stirred at 20° C. for 24 h, then H2O (0.4 mL) is added. The reaction mixture is evaporated and the residue purified by preparative HPLC to provide the title compound. The reaction mixture is stirred at 20° C. for 24 h The reaction mixture is evaporated the residue purified by preparative HPLC
Source ID: ord-3925a18c660d4ba7bf8c3fa196ebf96eConditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of CDI (178 mg, 1.1 mmol) in DMSO (5 mL) is added a solution of 2-(4-benzyl-piperidin-1-yl)-ethylamine (218 mg, 1 mmol) in DMSO (1 mL). The reaction mixture is stirred at 20° C. for 3 h. Methyl-(2-methyl-quinolin-4-yl)-amine (173 mg, 1 mmol) is added. To the resulting solution is added in a single portion NaHMDS (2 M in THF, 1.25 mL, 2.5 mmol). The reaction mixture is stirred at 20° C. for 24 h, then H2O (0.4 mL) is added. The reaction mixture is evaporated and the residue purified by preparative HPLC to provide the title compound. The reaction mixture is stirred at 20° C. for 24 h The reaction mixture is evaporated the residue purified by preparative HPLC
Source ID: ord-3925a18c660d4ba7bf8c3fa196ebf96eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: [2-(4-Benzyl-piperidin-1-yl)-ethyl]-carbamic acid tert-butyl ester (1.34 g, 4.2 mmol) is dissolved in CHCl3 (3 mL) and treated with TFA (3 mL) for 2 h at 20° C. The solvent is evaporated, the residue dissolved CH2Cl2 (100 mL) and washed with 1M aqueous NaOH (2×30 mL). The organic layer is dried (Na2SO4), filtered and concentrated to provide the title compound. The solvent is evaporated the residue dissolved CH2Cl2 (100 mL) washed with 1M aqueous NaOH (2×30 mL) The organic layer is dried (Na2SO4) filtered concentrated
Source ID: ord-613c097532794b6eb35e701bbccad6b1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: [2-(4-Benzyl-piperidin-1-yl)-ethyl]-carbamic acid tert-butyl ester (1.34 g, 4.2 mmol) is dissolved in CHCl3 (3 mL) and treated with TFA (3 mL) for 2 h at 20° C. The solvent is evaporated, the residue dissolved CH2Cl2 (100 mL) and washed with 1M aqueous NaOH (2×30 mL). The organic layer is dried (Na2SO4), filtered and concentrated to provide the title compound. The solvent is evaporated the residue dissolved CH2Cl2 (100 mL) washed with 1M aqueous NaOH (2×30 mL) The organic layer is dried (Na2SO4) filtered concentrated
Source ID: ord-613c097532794b6eb35e701bbccad6b1PubChem References
These sources are listed in the compound's public database record.
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