N,N-bis(prop-2-enyl)aniline

Conditions: temp:19.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of aniline (5.62 g, 60.36 mmol) in EtOH (200 ml) and water (50 ml) was added allyl bromide (17.33 g, 143.3 mmol) in one portion followed by solid Na2CO3 (6.69 g, 62.5 mmol). The yellow mixture was then heated under reflux for 17 h, left to cool to room temperature (19° C.) and the EtOH was removed under reduced pressure. The aqueous residue was extracted with Et2O (5×200 ml) and the combined organics were washed with brine (3×200 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a brown oil that was distilled over KOH pellets to give the title compound (7.81 g, 75%) as a pale yellow oil. The yellow mixture was then heated under reflux for 17 h left the EtOH was removed under reduced pressure The aqueous residue was extracted with Et2O (5×200 ml) the combined organics were washed with brine (3×200 ml) dried (Na2SO4) The solvent was removed under reduced pressure to give a brown oil that was distilled over KOH pellets

Conditions: temp:19.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of aniline (5.62 g, 60.36 mmol) in EtOH (200 ml) and water (50 ml) was added allyl bromide (17.33 g, 143.3 mmol) in one portion followed by solid Na2CO3 (6.69 g, 62.5 mmol). The yellow mixture was then heated under reflux for 17 h, left to cool to room temperature (19° C.) and the EtOH was removed under reduced pressure. The aqueous residue was extracted with Et2O (5×200 ml) and the combined organics were washed with brine (3×200 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a brown oil that was distilled over KOH pellets to give the title compound (7.81 g, 75%) as a pale yellow oil. The yellow mixture was then heated under reflux for 17 h left the EtOH was removed under reduced pressure The aqueous residue was extracted with Et2O (5×200 ml) the combined organics were washed with brine (3×200 ml) dried (Na2SO4) The solvent was removed under reduced pressure to give a brown oil that was distilled over KOH pellets