(4-butoxyphenyl)methanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 4-butoxybenzonitrile (4.6 g, 26.25 mmol) in Et2O (50 mL) was added lithium aluminum hydride (1.0 M in THF, 26.2 mL, 26.2 mmol) dropwise. The reaction was heated at reflux for 1 h and was cooled to room temperature. The reaction was carefully poured into water (50 mL) and was diluted with Et2O. The solids were removed by filtration through Celite with the aid of Et2O. The organic solution was washed with water followed by brine, dried (MgSO4), filtered, and concentrated in vacuo to provide 4-butoxybenzylamine (2.68 g). 1H NMR (400 MHz, CDCl3) δ 7.16 (m, 2H), 6.82 (m, 2H), 3.91 (m, 2H), 3.75 (s, 2H), 1.73 (m, 2H), 1.46 (m, 2H), 1.39 (m, 2H), 0.95 (t, 3H). The reaction was heated at reflux for 1 h The solids were removed by filtration through Celite with the aid of Et2O The organic solution was washed with water dried (MgSO4) filtered concentrated in vacuo

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

Procedure: To a solution of 4-butoxybenzonitrile (4.6 g, 26.25 mmol) in Et2O (50 mL) was added lithium aluminum hydride (1.0 M in THF, 26.2 mL, 26.2 mmol) dropwise. The reaction was heated at reflux for 1 h and was cooled to room temperature. The reaction was carefully poured into water (50 mL) and was diluted with Et2O. The solids were removed by filtration through Celite with the aid of Et2O. The organic solution was washed with water followed by brine, dried (MgSO4), filtered, and concentrated in vacuo to provide 4-butoxybenzylamine (2.68 g). 1H NMR (400 MHz, CDCl3) δ 7.16 (m, 2H), 6.82 (m, 2H), 3.91 (m, 2H), 3.75 (s, 2H), 1.73 (m, 2H), 1.46 (m, 2H), 1.39 (m, 2H), 0.95 (t, 3H). The reaction was heated at reflux for 1 h The solids were removed by filtration through Celite with the aid of Et2O The organic solution was washed with water dried (MgSO4) filtered concentrated in vacuo

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

Procedure: To a solution of 4-butoxybenzonitrile (4.6 g, 26.25 mmol) in Et2O (50 mL) was added lithium aluminum hydride (1.0 M in THF, 26.2 mL, 26.2 mmol) dropwise. The reaction was heated at reflux for 1 h and was cooled to room temperature. The reaction was carefully poured into water (50 mL) and was diluted with Et2O. The solids were removed by filtration through Celite with the aid of Et2O. The organic solution was washed with water followed by brine, dried (MgSO4), filtered, and concentrated in vacuo to provide 4-butoxybenzylamine (2.68 g). 1H NMR (400 MHz, CDCl3) δ 7.16 (m, 2H), 6.82 (m, 2H), 3.91 (m, 2H), 3.75 (s, 2H), 1.73 (m, 2H), 1.46 (m, 2H), 1.39 (m, 2H), 0.95 (t, 3H). The reaction was heated at reflux for 1 h The solids were removed by filtration through Celite with the aid of Et2O The organic solution was washed with water dried (MgSO4) filtered concentrated in vacuo

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

Procedure: To a solution of 4-butoxybenzonitrile (4.6 g, 26.25 mmol) in Et2O (50 mL) was added lithium aluminum hydride (1.0M in THF, 26.2 mL, 26.2 mmol) dropwise. The reaction was heated at reflux for 1 h and was cooled to room temperature. The reaction was carefully poured into water (50 mL) and was diluted with Et2O. The solids were removed by filtration through Celite with the aid of Et2O. The organic solution was washed with water followed by brine, dried (MgSO4), filtered, and concentrated in vacuo to provide 4-butoxybenzylamine (2.68 g). 1H NMR (400 MHz, CDCl3) δ 7.16 (m, 2H), 6.82 (m, 2H), 3.91 (m, 2H), 3.75 (s, 2H), 1.73 (m, 2H), 1.46 (m, 2H), 1.39 (m, 2H), 0.95 (t, 3H). The reaction was heated at reflux for 1 h The solids were removed by filtration through Celite with the aid of Et2O The organic solution was washed with water dried (MgSO4) filtered concentrated in vacuo

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

Procedure: To a solution of 4-butoxybenzonitrile (4.6 g, 26.25 mmol) in Et2O (50 mL) was added lithium aluminum hydride (1.0 M in THF, 26.2 mL, 26.2 mmol) dropwise. The reaction was heated at reflux for 1 h and was cooled to room temperature. The reaction was carefully poured into water (50 mL) and was diluted with Et2O. The solids were removed by filtration through Celite with the aid of Et2O. The organic solution was washed with water followed by brine, dried (MgSO4), filtered, and concentrated in vacuo to provide 4-butoxybenzylamine (2.68 g). 1H NMR (400 MHz, CDCl3) δ7.16 (m, 2H), 6.82 (m, 2H), 3.91 (m, 2H), 3.75 (s, 2H), 1.73 (m, 2H), 1.46 (m, 2H), 1.39 (m, 2H), 0.95 (t, 3H). The reaction was heated at reflux for 1 h The solids were removed by filtration through Celite with the aid of Et2O The organic solution was washed with water dried (MgSO4) filtered concentrated in vacuo

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

Procedure: To a solution of 4-butoxybenzonitrile (4.6 g, 26.25 mmol) in Et2O (50 mL) was added lithium aluminum hydride (1.0 M in THF, 26.2 mL, 26.2 mmol) dropwise. The reaction was heated at reflux for 1 h and was cooled to room temperature. The reaction was carefully poured into water (50 mL) and was diluted with Et2O. The solids were removed by filtration through Celite with the aid of Et2O. The organic solution was washed with water followed by brine, dried (MgSO4), filtered, and concentrated in vacuo to provide 4-butoxybenzylamine (2.68 g). 1H NMR (400 MHz, CDCl3) δ 7.16 (m, 2H), 6.82 (m, 2H), 3.91 (m, 2H), 3.75 (s, 2(m, 2H), 1.46 (m, 2H), 1.39 (m, 2H), 0.95 (t, 3H). The reaction was heated at reflux for 1 h The solids were removed by filtration through Celite with the aid of Et2O The organic solution was washed with water dried (MgSO4) filtered concentrated in vacuo

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

Procedure: To a solution of 4-butoxybenzonitrile (4.6 g, 26.25 mmol) in Et2O (50 mL) was added lithium aluminum hydride (1.0 M in THF, 26.2 mL, 26.2 mmol) dropwise. The reaction was heated at reflux for 1 h and was cooled to room temperature. The reaction was carefully poured into water (50 mL) and was diluted with Et2O. The solids were removed by filtration through Celite with the aid of Et2O. The organic solution was washed with water followed by brine, dried (MgSO4), filtered, and concentrated in vacuo to provide 4-butoxybenzylamine (2.68 g). 1H NMR (400 MHz, CDCl3) δ 7.16 (m, 2H), 6.82 (m, 2H), 3.91 (m, 2H), 3.75 (s, 2H), 1.73 (m, 2H), 1.46 (m, 2H), 1.39 (m, 2H), 0.95 (t, 3H). The reaction was heated at reflux for 1 h The solids were removed by filtration through Celite with the aid of Et2O The organic solution was washed with water dried (MgSO4) filtered concentrated in vacuo

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

Procedure: To a solution of 4-butoxybenzonitrile (4.6 g, 26.25 mmol) in Et2O (50 mL) was added lithium aluminum hydride (1.0 M in THF, 26.2 mL, 26.2 mmol) dropwise. The reaction was heated at reflux for 1 h and was cooled to room temperature. The reaction was carefully poured into water (50 mL) and was diluted with Et2O. The solids were removed by filtration through Celite with the aid of Et2O. The organic solution was washed with water followed by brine, dried (MgSO4), filtered, and concentrated in vacuo to provide 4-butoxybenzylamine (2.68 g). 1H NMR (400 MHz, CDCl3) δ 7.16 (m, 2H), 6.82 (m, 2H), 3.91 (m, 2H), 3.75 (s, 2H), 1.73 (m, 2H), 1.46 (m, 2H), 1.39 (m, 2H), 0.95 (t, 3H). The reaction was heated at reflux for 1 h The solids were removed by filtration through Celite with the aid of Et2O The organic solution was washed with water dried (MgSO4) filtered concentrated in vacuo