N-(2-phenylethyl)butan-1-amine

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

Procedure: 2-Phenethylamine (12.5 mL, 12.1 g, 99.5 mmol), butyraldehyde (13.2 mL, 10.8 g, 150 mmol), and 3 Å molecular sieves were stirred at 50 ° C. for 1 h, then at RT for 5.5 h. The reaction was then diluted with CH2Cl2, filtered through celite, then concentrated to an oil. That oil was dissolved in absolute EtOH (150 mL-previously cooled to 0 ° C.), and NaBH4 (5.7 g, 150 mmol) was added. The reaction was stirred at RT overnight, concentrated, partitioned between water and Et2O, then the organic layer was washed with water and brine. After drying over Na2SO4, filtration, and concentration, the compound was purified by vacuum distillation using a 6″ Vigeraux column (98-100° C./9 mm). Recovered 8.2 g (46%). filtered through celite concentrated to an oil That oil was dissolved in absolute EtOH (150 mL- was added concentrated partitioned between water and Et2O the organic layer was washed with water and brine After drying over Na2SO4, filtration, and concentration the compound was purified by vacuum distillation Vigeraux column (98-100° C./9 mm) Recovered 8.2 g (46%)

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

Procedure: 2-Phenethylamine (12.5 mL, 12.1 g, 99.5 mmol), butyraldehyde (13.2 mL, 10.8 g, 150 mmol), and 3 Å molecular sieves were stirred at 50 ° C. for 1 h, then at RT for 5.5 h. The reaction was then diluted with CH2Cl2, filtered through celite, then concentrated to an oil. That oil was dissolved in absolute EtOH (150 mL-previously cooled to 0 ° C.), and NaBH4 (5.7 g, 150 mmol) was added. The reaction was stirred at RT overnight, concentrated, partitioned between water and Et2O, then the organic layer was washed with water and brine. After drying over Na2SO4, filtration, and concentration, the compound was purified by vacuum distillation using a 6″ Vigeraux column (98-100° C./9 mm). Recovered 8.2 g (46%). filtered through celite concentrated to an oil That oil was dissolved in absolute EtOH (150 mL- was added concentrated partitioned between water and Et2O the organic layer was washed with water and brine After drying over Na2SO4, filtration, and concentration the compound was purified by vacuum distillation Vigeraux column (98-100° C./9 mm) Recovered 8.2 g (46%)

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

Procedure: 2-Phenethylamine (12.5 mL, 12.1 g, 99.5 mmol), butyraldehyde (13.2 mL, 10.8 g, 150 mmol), and 3 Å molecular sieves were stirred at 50 ° C. for 1 h, then at RT for 5.5 h. The reaction was then diluted with CH2Cl2, filtered through celite, then concentrated to an oil. That oil was dissolved in absolute EtOH (150 mL-previously cooled to 0 ° C.), and NaBH4 (5.7 g, 150 mmol) was added. The reaction was stirred at RT overnight, concentrated, partitioned between water and Et2O, then the organic layer was washed with water and brine. After drying over Na2SO4, filtration, and concentration, the compound was purified by vacuum distillation using a 6″ Vigeraux column (98-100° C./9 mm). Recovered 8.2 g (46%). filtered through celite concentrated to an oil That oil was dissolved in absolute EtOH (150 mL- was added concentrated partitioned between water and Et2O the organic layer was washed with water and brine After drying over Na2SO4, filtration, and concentration the compound was purified by vacuum distillation Vigeraux column (98-100° C./9 mm) Recovered 8.2 g (46%)