N-[(4-bromo-3-methylphenyl)methyl]-3-methylbutan-1-amine

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (4-bromo-3-methyl-benzyl)-(3-methyl-butyl)-amine (I-2b: 13.7 g) was dissolved in 100 mL of ethyl acetate and treated with 200 mL of a saturated aqueous sodium bicarbonate solution and di-tert-butyl-carbonate (14.3 g, 65.5 mmol). The reaction mixture was stirred at 50° C. for 2 hours before cooling to room temperature and the aqueous phase extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated to provide the title compound (I-2c). before cooling to room temperature the aqueous phase extracted with ethyl acetate The combined organic phases were washed with brine dried over sodium sulfate filtered concentrated

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

Procedure: 4-bromo-3-methyl-benzaldehyde (2a: 10.20 g, 51.2 mmol) was dissolved in methanol (150 ml) before adding isoamyl amine (6.75 g, 77 mmol). After stirring overnight at room temperature, sodium borohydride (5.9 g, 154 mmol) was added. After stirring for 1 hour at room temperature, the reaction was quenched using concentrated (37%) hydrochloric acid and the volatiles were removed with a rotary evaporator under reduced pressure. The resulting residue was made basic with a 2 N aqueous sodium hydroxide solution and extracted twice with ethyl acetate. The combined organics were washed with a saturated aqueous sodium bicarbonate solution and dried over sodium sulfate, filtered and concentrated under reduced pressure to provide 13.7 g of the title compound (I-2b). After stirring for 1 hour at room temperature the reaction was quenched using concentrated (37%) hydrochloric acid the volatiles were removed with a rotary evaporator under reduced pressure extracted twice with ethyl acetate The combined organics were washed with a saturated aqueous sodium bicarbonate solution dried over sodium sulfate filtered concentrated under reduced pressure