No renderable structure data available
COC(=O)CC1CN(CCN1)CC2=CC=CC=C2Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | methyl 2-(4-benzylpiperazin-2-yl)acetate |
|---|---|
| IUPAC Name | — |
| CAS Number | 141856-12-4 |
| Database ID | 15665466 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
methyl 2-(4-benzylpiperazin-2-yl)acetate (CAS 141856-12-4) 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 15665466
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-eb64868b83c64cfea73ac168fdfb68a2Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-eb64868b83c64cfea73ac168fdfb68a2Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Example 12C (625 mg, 4.03 mmol) in acetonitrile (5 mL) was added 1-fluoro-4-methyl-2-nitrobenzene (1.00 g, 4.03 mmol) and potassium carbonate (1.11 g, 805 mmol). The reaction was heated in an oil bath at 60° C. overnight. The solution was concentrated onto silica gel and purified via flash chromatography (0-100% ethyl acetate/hexanes) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.55-7.60 (m, 1H), 7.22-7.43 (m, 7H), 3.55-3.65 (m, 1H), 3.41-3.59 (m, 2H), 3.36 (s, 3H), 3.09-3.21 (m, 1H), 2.77-2.88 (m, 1H), 2.22-2.62 (m, 7H); MS (APCI+) m/z 384 (M+H)+. The solution was concentrated onto silica gel purified via flash chromatography (0-100% ethyl acetate/hexanes)
Source ID: ord-5d7c561de0d4476c8eb9c7949a97cb21Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Example 12C (0.907 g, 3.65 mmol) in acetonitrile (11.69 mL) was added 2-fluoro-4-methoxy-1-nitrobenzene (0.50 g, 2.92 mmol) and potassium carbonate (2.019 g, 14.61 mmol) in water (2.92 mL) followed by 18-crown-6 (0.039 g, 0.146 mmol), and the mixture was heated with an oil bath at 90° C. (reflux) for 24 hours. The solvent was evaporated and water was added followed by dichloromethane. The water phase was washed three times with dichloromethane to remove starting material and then acidified with 1 N HCl until pH=1. The acid product was extracted three times with dichloromethane, dried quickly with sodium sulfate and concentrated to give the title compound. MS (ESI) m/z 386.1 (M+H)+. (reflux) for 24 hours The solvent was evaporated water was added The water phase was washed three times with dichloromethane to remove The acid product was extracted three times with dichloromethane dried quickly with sodium sulfate concentrated
Source ID: ord-b1c81f68774a4c8abfd5117526424148Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Example 12B (160 g, 326 mmol) in methanol (652 mL) was added 4 M HCl in dioxane (408 mL, 1630 mmol) and the mixture was heated at 50° C. for 3 hours. The solvent was then evaporated and water was added. A solid precipitates. The water layer was decanted and washed once with ethyl acetate. The solid was dissolved in ethyl acetate and extracted with water once. The water layers were combined and treated with 1 N NaOH (1 L) until pH=10. The free amine was extracted twice with dichloromethane, dried over sodium sulfate and concentrated to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.34-7.20 (m, 5H), 3.57 (s, 3H), 3.42 (q, J=13.4 Hz, 2H), 2.96 (qd, J=2.7 Hz, 6.9 Hz, 1H), 2.78 (dt, J=2.9 Hz, 11.9 Hz, 1H), 2.69-2.60 (m, 2H), 2.55 (d, J=10.8 Hz, 1H), 2.30 (dd, J=3.2 Hz, 6.7 Hz, 2H), 1.92 (td, J=2.8 Hz, 10.6 Hz, 1H), 1.68 (t, J=10.0 Hz, 1H); MS (ESI) m/z 249.0 (M+H)+. The solvent was then evaporated water was added A solid precipitates The water layer was decanted washed once with ethyl acetate The solid was dissolved in ethyl acetate extracted with water once treated with 1 N NaOH (1 L) until pH=10 The free amine was extracted twice with dichloromethane dried over sodium sulfate concentrated
Source ID: ord-84abd51821bc4e34a4a6de742b892b3eConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Example 12B (160 g, 326 mmol) in methanol (652 mL) was added 4 M HCl in dioxane (408 mL, 1630 mmol) and the mixture was heated at 50° C. for 3 hours. The solvent was then evaporated and water was added. A solid precipitates. The water layer was decanted and washed once with ethyl acetate. The solid was dissolved in ethyl acetate and extracted with water once. The water layers were combined and treated with 1 N NaOH (1 L) until pH=10. The free amine was extracted twice with dichloromethane, dried over sodium sulfate and concentrated to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.34-7.20 (m, 5H), 3.57 (s, 3H), 3.42 (q, J=13.4 Hz, 2H), 2.96 (qd, J=2.7 Hz, 6.9 Hz, 1H), 2.78 (dt, J=2.9 Hz, 11.9 Hz, 1H), 2.69-2.60 (m, 2H), 2.55 (d, J=10.8 Hz, 1H), 2.30 (dd, J=3.2 Hz, 6.7 Hz, 2H), 1.92 (td, J=2.8 Hz, 10.6 Hz, 1H), 1.68 (t, J=10.0 Hz, 1H); MS (ESI) m/z 249.0 (M+H)+. The solvent was then evaporated water was added A solid precipitates The water layer was decanted washed once with ethyl acetate The solid was dissolved in ethyl acetate extracted with water once treated with 1 N NaOH (1 L) until pH=10 The free amine was extracted twice with dichloromethane dried over sodium sulfate concentrated
Source ID: ord-84abd51821bc4e34a4a6de742b892b3eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using an analogous procedure to that described in Example 2, methyl 2-(1-benzylpiperazin-3-yl)acetate (J. Chem. Soc. Perkin I, 1992, 1035) was reacted with 2-naphthylsulphonyl chloride to give methyl 2-[4-benzyl-1-(2-naphthylsulphonyl)piperazin-2-yl]acetate in 90% yield.
Source ID: ord-f25d3b07cdc14141b3af475f39ab9bc5Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Example 12C (625 mg, 4.03 mmol) in acetonitrile (5 mL) was added 1-fluoro-4-methyl-2-nitrobenzene (1.00 g, 4.03 mmol) and potassium carbonate (1.11 g, 805 mmol). The reaction was heated in an oil bath at 60° C. overnight. The solution was concentrated onto silica gel and purified via flash chromatography (0-100% ethyl acetate/hexanes) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.55-7.60 (m, 1 H), 7.22-7.43 (m, 7 H), 3.55-3.65 (m, 1 H), 3.41-3.59 (m, 2 H), 3.36 (s, 3 H), 3.09-3.21 (m, 1 H), 2.77-2.88 (m, 1 H), 2.22-2.62 (m, 7 H); MS (APCI+) m/z 384 (M+H)+. The solution was concentrated onto silica gel purified via flash chromatography (0-100% ethyl acetate/hexanes)
Source ID: ord-fa709513340d4c7f96e57e27ea9a3b73Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Example 12C (0.907 g, 3.65 mmol) in acetonitrile (11.69 mL) was added 2-fluoro-4-methoxy-1-nitrobenzene (0.50 g, 2.92 mmol) and potassium carbonate (2.019 g, 14.61 mmol) in water (2.92 mL) followed by 18-crown-6 (0.039 g, 0.146 mmol), and the mixture was heated with an oil bath at 90° C. (reflux) for 24 hours. The solvent was evaporated and water was added followed by dichloromethane. The water phase was washed three times with dichloromethane to remove starting material and then acidified with 1 N HCl until pH=1. The acid product was extracted three times with dichloromethane, dried quickly with sodium sulfate and concentrated to give the title compound. MS (ESI) m/z 386.1 (M+H)+. (reflux) for 24 hours The solvent was evaporated water was added The water phase was washed three times with dichloromethane to remove The acid product was extracted three times with dichloromethane dried quickly with sodium sulfate concentrated
Source ID: ord-9880190aec6b457b8577ae8afd55e028Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Example 12B (160 g, 326 mmol) in methanol (652 mL) was added 4 M HCl in dioxane (408 mL, 1630 mmol) and the mixture was heated at 50° C. for 3 hours. The solvent was then evaporated and water was added. A solid precipitates. The water layer was decanted and washed once with ethyl acetate. The solid was dissolved in ethyl acetate and extracted with water once. The water layers were combined and treated with 1 N NaOH (1 L) until pH=10. The free amine was extracted twice with dichloromethane, dried over sodium sulfate and concentrated to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.34-7.20 (m, 5H), 3.57 (s, 3H), 3.42 (q, J=13.4 Hz, 2H), 2.96 (qd, J=2.7 Hz, 6.9 Hz, 1H), 2.78 (dt, J=2.9 Hz, 11.9 Hz, 1H), 2.69-2.60 (m, 2H), 2.55 (d, J=10.8 Hz, 1H), 2.30 (dd, J=3.2 Hz, 6.7 Hz, 2H), 1.92 (td, J=2.8 Hz, 10.6 Hz, 1H), 1.68 (t, J=10.0 Hz, 1H); MS (ESI) m/z 249.0 (M+H)+. The solvent was then evaporated water was added A solid precipitates The water layer was decanted washed once with ethyl acetate The solid was dissolved in ethyl acetate extracted with water once treated with 1 N NaOH (1 L) until pH=10 The free amine was extracted twice with dichloromethane dried over sodium sulfate concentrated
Source ID: ord-1def8d82345c4225b160100ecd33e789Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Example 12C (625 mg, 4.03 mmol) in acetonitrile (5 mL) was added 1-fluoro-4-methyl-2-nitrobenzene (1.00 g, 4.03 mmol) and potassium carbonate (1.11 g, 805 mmol). The reaction was heated in an oil bath at 60° C. overnight. The solution was concentrated onto silica gel and purified via flash chromatography (0-100% ethyl acetate/hexanes) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.55-7.60 (m, 1H), 7.22-7.43 (m, 7H), 3.55-3.65 (m, 1H), 3.41-3.59 (m, 2H), 3.36 (s, 3H), 3.09-3.21 (m, 1H), 2.77-2.88 (m, 1H), 2.22-2.62 (m, 7H); MS (APCI+) m/z 384 (M+H)+. The solution was concentrated onto silica gel purified via flash chromatography (0-100% ethyl acetate/hexanes)
Source ID: ord-3a3745ed3ac6495e872012e3c04ccd07Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Example 12C (0.907 g, 3.65 mmol) in acetonitrile (11.69 mL) was added 2-fluoro-4-methoxy-1-nitrobenzene (0.50 g, 2.92 mmol) and potassium carbonate (2.019 g, 14.61 mmol) in water (2.92 mL) followed by 18-crown-6 (0.039 g, 0.146 mmol), and the mixture was heated with an oil bath at 90° C. (reflux) for 24 hours. The solvent was evaporated and water was added followed by dichloromethane. The water phase was washed three times with dichloromethane to remove starting material and then acidified with 1N HCl until pH=1. The acid product was extracted three times with dichloromethane, dried quickly with sodium sulfate and concentrated to give the title compound. MS (ESI) m/z 386.1 (M+H)+. (reflux) for 24 hours The solvent was evaporated water was added The water phase was washed three times with dichloromethane to remove The acid product was extracted three times with dichloromethane dried quickly with sodium sulfate concentrated
Source ID: ord-1a25bfed7a854408a47cbd41ae7cce3dPubChem References
These sources are listed in the compound's public database record.
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