反应详情

温度

30 °C

Prepare a solution of 0.83 kg (21.9 mol) sodium borohydride in 16.6 kg NMP. Add 31.9 kg N-(propylidene)-1H-indol-1-amine as a 19.7% solution in n-heptane (36.5 mol) and additional 7.7 kg n-Heptane. Prepare a solution of 1.32 kg (21.9 mol) glacial acetic acid in 2.8 kg n-heptane. Add the acetic acid solution over a period of about 30 min at 30° C. to the sodium borohydride solution using a pump. Immediately hydrogen evolution will occur. Rinse the pump with 2 kg n-heptane. Stir the reaction mixture at 30° C. until completion of the reaction (˜1 h). The reaction mixture is then worked-up by adding 20 L water. No or only minimal foaming is observed during the addition of water. Stir the mixture over night and separate the phases. Add 0.9 kg HCl (30%) and 3.4 kg water to the n-heptane phase, check whether the pH is below 1. Add additional amounts of HCl if necessary to adjust the pH around 1. Heat this mixture to 75° C. internal temperature for ˜2 h. Cool the mixture to 25° C. in order to control the residual hydrogen that is evolved. If no more residual hydrogen is evolved, add additional 20.3 kg water, and adjust pH to a level >7 with NaOH (33%). Separate the phases and wash the n-heptane phase with 20.3 kg water. Evaporate the n-heptane phase to dryness. This results in 5.84 kg N-propyl-1H-indol-1-amine (82.6%) as a brown liquid.

1. washRinse the pump with 2 kg n-heptane
2. customuntil completion of the reaction (˜1 h)
3. stirringStir the mixture over night
4. customseparate the phases
5. additionAdd 0.9 kg HCl (30%) and 3.4 kg water to the n-heptane phase
6. additionAdd additional amounts of HCl if necessary
7. temperatureHeat this mixture to 75° C. internal temperature for ˜2 h
8. temperatureCool the mixture to 25° C. in order
9. additionadd additional 20.3 kg water
10. customSeparate the phases
11. washwash the n-heptane phase with 20.3 kg water
12. customEvaporate the n-heptane phase to dryness
13. customThis results in 5.84 kg N-propyl-1H-indol-1-amine (82.6%) as a brown liquid