No renderable structure data available
C1CNCCC1CC2=CC=C(C=C2)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-(piperidin-4-ylmethyl)aniline |
|---|---|
| IUPAC Name | — |
| CAS Number | 37581-35-4 |
| Database ID | 10997824 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-(piperidin-4-ylmethyl)aniline (CAS 37581-35-4) 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 10997824
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-6530176a5aeb423e87ec34a74a5e0db8Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-124d461bf7814789a4d073053512facfConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-(piperidin-4-ylmethyl)-phenylamine (0.57 g, 3 mmol) in dichloromethane (20 mL) was cooled in an ice bath under nitrogen atmosphere. Isopropyl isocyanate (0.28 g, 3.3 mmol) was added dropwise to the solution and stirred at ice bath temperature for 30 minutes. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic extracts were washed with water and brine, dried, and solvents removed in vacuo. The crude product was chromatographed on silica gel, eluting with 2% methanol/dichloromethane containing 0.01% ammonium hydroxide, to give 4-(1-isopropylaminocarbonylpiperidin-4-ylmethyl)-phenylamine (0.66 g, 80%) as a gum. The reaction mixture was quenched with water extracted with dichloromethane The combined organic extracts were washed with water and brine dried solvents removed in vacuo The crude product was chromatographed on silica gel eluting with 2% methanol/dichloromethane containing 0.01% ammonium hydroxide
Source ID: ord-65d37e6e0ef14b2895da35145511fc7eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-(piperidin-4-ylmethyl)-phenylamine (0.57 g, 3 mmol) in dichloromethane (20 mL) was cooled in an ice bath under nitrogen atmosphere. Isopropyl isocyanate (0.28 g, 3.3 mmol) was added dropwise to the solution and stirred at ice bath temperature for 30 minutes. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic extracts were washed with water and brine, dried, and solvents removed in vacuo. The crude product was chromatographed on silica gel, eluting with 2% methanol/dichloromethane containing 0.01% ammonium hydroxide, to give 4-(1-isopropylaminocarbonylpiperidin-4-ylmethyl)-phenylamine (0.66 g, 80%) as a gum. The reaction mixture was quenched with water extracted with dichloromethane The combined organic extracts were washed with water and brine dried solvents removed in vacuo The crude product was chromatographed on silica gel eluting with 2% methanol/dichloromethane containing 0.01% ammonium hydroxide
Source ID: ord-65d37e6e0ef14b2895da35145511fc7eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4-(4-nitrobenzyl)pyridine (12.85 g, 60 mmol), platinum(IV) oxide (1.0 g), 12N hydrochloric acid (5 ml, 60 mmol), water (5 ml) in ethanol (200 ml) was hydrogenated at 40 psi in a Parr apparatus for 12 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with cold water and basified with 10% sodium hydroxide solution. The resulting mixture was extracted into ethyl acetate. The combined organic extracts were washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The residue on crystallization from ethyl acetate/hexanes gave 4-(piperidin-4-ylmethyl)-phenylamine (9.85 g, 86%) as a white crystalline solid, m.p. 110-113° C. The reaction mixture was concentrated in vacuo the residue was diluted with cold water and basified with 10% sodium hydroxide solution The resulting mixture was extracted into ethyl acetate The combined organic extracts were washed with water and brine dried (Na2SO4) concentrated in vacuo The residue on crystallization from ethyl acetate/hexanes
Source ID: ord-2ad215af58b7429aba2f804a7be8fa31Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-(piperidin-4-ylmethyl)-phenylamine (0.57 g, 3 mmol) in dicholoromethane (20 mL) was cooled in an ice bath under nitrogen atmosphere. Isopropyl isocyanate (0.28 g, 3.3 mmol) was added dropwise to the solution and stirred at ice bath temperature for 30 minutes. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic extracts were washed with water and brine, dried, and solvents removed in vacuo. The crude product was chromatographed on silica gel, eluting with 2% methanovdichloromethane containing 0.01% ammonium hydroxide, to give 4-(1-isopropylaminocarbonylpiperidin-4-ylmethyl)-phenylamine (0.66 g, 80%) as a gum. The reaction mixture was quenched with water extracted with dichloromethane The combined organic extracts were washed with water and brine dried solvents removed in vacuo The crude product was chromatographed on silica gel eluting with 2% methanovdichloromethane containing 0.01% ammonium hydroxide
Source ID: ord-f6d9298b57e44ed78c4b44bac8221de5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4-(4-nitrobenzyl)pyridine (12.85 g, 60 mmol), platinum(IV) oxide (1.0 g), 12N hydrochloric acid (5 ml, 60 mmol), water (5 ml) in ethanol (200 ml) was hydrogenated at 40 psi in a Parr apparatus for 12 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with cold water and basified with 10% sodium hydroxide solution. The resulting mixture was extracted into ethyl acetate. The combined organic extracts were washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The residue on crystallization from ethyl acetate/hexanes gave 4-(piperidin-4-ylmethyl)-phenylamine (9.85 g, 86%) as a white crystalline solid, m.p. 110–113° C. The reaction mixture was concentrated in vacuo the residue was diluted with cold water and basified with 10% sodium hydroxide solution The resulting mixture was extracted into ethyl acetate The combined organic extracts were washed with water and brine dried (Na2SO4) concentrated in vacuo The residue on crystallization from ethyl acetate/hexanes
Source ID: ord-2e561e2e750c4a5b86f2845f87eaf4faConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4-(4-nitrobenzyl)pyridine (12.85 g, 60 mmol), platinum(IV) oxide (1.0 g), 12N hydrochloric acid (5 ml, 60 mmol), water (5 ml) in ethanol (200 ml) was hydrogenated at 40 psi in a Parr apparatus for 12 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with cold water and basified with 10% sodium hydroxide solution. The resulting mixture was extracted into ethyl acetate. The combined organic extracts were washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The residue on crystallization from ethyl acetate/hexanes gave 4-(piperidin-4-ylmethyl)-phenylamine (9.85 g, 86%) as a white crystalline solid, m.p. 110–113° C. The reaction mixture was concentrated in vacuo the residue was diluted with cold water and basified with 10% sodium hydroxide solution The resulting mixture was extracted into ethyl acetate The combined organic extracts were washed with water and brine dried (Na2SO4) concentrated in vacuo The residue on crystallization from ethyl acetate/hexanes
Source ID: ord-2e561e2e750c4a5b86f2845f87eaf4faConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-(piperidin-4-ylmethyl)-phenylamine (0.57 g, 3 mmol) in dicholoromethane (20 mL) was cooled in an ice bath under nitrogen atmosphere. Isopropyl isocyanate (0.28 g, 3.3 mmol) was added dropwise to the solution and stirred at ice bath temperature for 30 minutes. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic extracts were washed with water and brine, dried, and solvents removed in vacua. The crude product was chromatographed on silica gel, eluting with 2% methanol/dichloromethane containing 0.01% ammonium hydroxide, to give 4-(1-isopropylaminocarbonylpiperidin-4-ylmethyl)-phenylamine (0.66 g, 80%) as a gum. The reaction mixture was quenched with water extracted with dichloromethane The combined organic extracts were washed with water and brine dried solvents removed in vacua The crude product was chromatographed on silica gel eluting with 2% methanol/dichloromethane containing 0.01% ammonium hydroxide
Source ID: ord-e239ed6d5fbb4eebb0a96d4d0c1ec0f0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4-(4-nitrobenzyl)pyridine (12.85 g, 60 mmol), platinum(IV) oxide (1.0 g), 12N hydrochloric acid (5 ml, 60 mmol), water (5 ml) in ethanol (200 ml) was hydrogenated at 40 psi in a Parr apparatus for 12 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with cold water and basified with 10% sodium hydroxide solution. The resulting mixture was extracted into ethyl acetate. The combined organic extracts were washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The residue on crystallization from ethyl acetate/hexanes gave 4-(piperidin-4-ylmethyl)-phenylamine (9.85 g, 86%) as a white crystalline solid, m.p. 110-113° C. The reaction mixture was concentrated in vacuo the residue was diluted with cold water and basified with 10% sodium hydroxide solution The resulting mixture was extracted into ethyl acetate The combined organic extracts were washed with water and brine dried (Na2SO4) concentrated in vacuo The residue on crystallization from ethyl acetate/hexanes
Source ID: ord-1c56253fd1cd4e318801626525f419b7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4-(4-nitrobenzyl)pyridine (12.85 g, 60 mmol), platinum(IV) oxide (1.0 g), 12N hydrochloric acid (5 ml, 60 mmol), water (5 ml) in ethanol (200 ml) was hydrogenated at 40 psi in a Parr apparatus for 12 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with cold water and basified with 10% sodium hydroxide solution. The resulting mixture was extracted into ethyl acetate. The combined organic extracts were washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The residue on crystallization from ethyl acetate/hexanes gave 4-(piperidin-4-ylmethyl)-phenylamine (9.85 g, 86%) as a white crystalline solid, m.p. 110-113° C. The reaction mixture was concentrated in vacuo the residue was diluted with cold water and basified with 10% sodium hydroxide solution The resulting mixture was extracted into ethyl acetate The combined organic extracts were washed with water and brine dried (Na2SO4) concentrated in vacuo The residue on crystallization from ethyl acetate/hexanes
Source ID: ord-1c56253fd1cd4e318801626525f419b7Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6530176a5aeb423e87ec34a74a5e0db8PubChem References
These sources are listed in the compound's public database record.
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