反应详情

温度

20 °C

A mixture of 38 g of 3-dimethylaminomethyl-5-fluoroindole (0.198 mole; cf. Hoffman et al. J. Heterocyclic Chem. 2, 298 [1965]; of the 5-fluorogramine therein) in 500 ml of methanol was prepared. Then a solution of 25.7 g of KCN (0.396 mole) in 50 ml of water was added, with stirring. The stirred mixture was cooled to 20° C. and 34.6 ml of methyl iodide (0.556 mole) was added over a 20 minute period. The mixture was then stirred about 20° C. for 16 hours. The solvent was removed by evaporation and the residue was partitioned between ether and water. The ether portion was washed with water, 5% HCl, saturated NaHCO3 solution, water, and brine, dried over MgSO4 and evaporated to leave a liquid residue. This residue was distilled at reduced pressure in a Kugelrohr apparatus. The fraction distilling at 134°-140° C. and 0.3 to 0.1 Torr was collected and crystallized from ethyl acetate-petroleum ether, mp. 58°-59°, yield 5.3 g (44% theory).

1. stirringThe mixture was then stirred about 20° C. for 16 hours
2. customThe solvent was removed by evaporation
3. customthe residue was partitioned between ether and water
4. washThe ether portion was washed with water, 5% HCl, saturated NaHCO3 solution, water, and brine
5. dry with materialdried over MgSO4
6. customevaporated
7. customto leave a liquid residue
8. distillationThis residue was distilled at reduced pressure in a Kugelrohr apparatus
9. distillationThe fraction distilling at 134°-140° C.
10. custom0.3 to 0.1 Torr was collected
11. customcrystallized from ethyl acetate-petroleum ether, mp. 58°-59°, yield 5.3 g (44% theory)