Hydrochloric Acid → N-[2-(4-chlorophenyl)ethyl]-N-heptylamine

Participants

Reaction Conditions

Reaction Steps

2-(4-Chlorophenyl)-N-heptylacetamide (1.045 g, 3.902 mmol) was dissolved in THF (10 ml) and was cooled to 0° C. under argon atmosphere. (Methylthio)methane compound with borane (1:1) (0.741 g, 9.756 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 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 flashcromatography (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 was pooled and the EtOAc was removed by evaporation to give 0.609 g of N-[2-(4-chlorophenyl)ethyl]-N-heptylamine (yield 61.5%).

Provenance & Evidence