反应详情

2-(4-Chlorophenyl)-N-heptylacetamide (0.886 g, 3.797 mmol) was dissolved in THF (10 ml) and was cooled to zero degrees under argon atmosphere. (Methylthio)methane compound with borane (1:1) (0.741 g, 9.755 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 chromatography (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 0.609 g of N-[2-(4-chlorophenyl)ethyl]-N-heptylamine (yield 61.5%).

1. temperaturewas cooled to zero degrees under argon atmosphere
2. temperaturethe mixture was refluxed for 5 hours
3. customThe solvent was removed by evaporation
4. additionEtOAc (20 ml) was added
5. washthe organic phase was washed with K2CO3 (2M, 2×20 ml)
6. customThe crude was purified by flash chromatography (
7. concentrationthe EtOAc concentration
8. temperaturewas increased to 100%, (silica gel 60 0.004-0.063 mm)
9. additionThe product containing fractions
10. customthe EtOAc was removed by evaporation