Hydrochloric Acid → N-[2-(2-methoxyphenyl)ethyl]heptan-1-amine

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Reaction Steps

N-Heptyl-2-(2-methoxyphenyl)acetamide (2.00 g, 7.594 mmol) was dissolved in THF (10 ml) and was cooled to zero degrees under argon atmosphere. (Methylthio)methane compound with borane (1:1) (1.442 g, 18.984 mmol) was added and the mixture was refluxed for 5 hours. After the mixture was cooled to room temperature, 5 ml HCl (10%) was gently added and the mixture was stirred overnight. The solvent was removed by evaporation. EtOAc (20 ml) was added and the organic phase was washed with K2CO3 (2M, 2×20 ml). The crude was purified by flash cromatography (started with isocratic heptane/EtOAc 50/50 and then the EtOAc concentration was increased to 100%, (silica gel 60 0.004-0.063 mm). The product containing fractions were pooled and the EtOAc was removed by evaporation to give 1.037 g of N-[2-(2-methoxyphenyl)ethyl]heptan-1-amine (yield 54.8%).

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