Sodium Hydroxide → 2-{[2-(1H-Indol-3-yl)ethyl]amino}ethan-1-ol

Temperature

-10 °C

398 g of the product of Step A were dissolved in 4 liters of tetrahydrofuran cooled to +10° C. and while maintaining this temperature, 400 g of 25% sodium diethyl dihydroaluminate in toluene were introduced. The mixture was stirred for 90 minutes while allowing the temperture to rise to 17° C. The medium was cooled to -10° C. and 400 ml of sodium hydroxide solution in 1200 ml of water were introduced over 80 minutes while keeping the temperature at 0° C. during the introduction. The mixture was stirred for 2 hours at +10° C. then allowed to rise to ambient temperature for 16 hours with slower stirring. After decanting, the organic phase was washed with water and the wash water was extracted with ethyl acetate and methylene chloride. The combined organic phases were diluted with methylene chloride and dried, and the solvents were expelled at 40° C. under reduced pressure. The residue was triturated in 1300 ml of ethyl acetate for one hour, separated, washed with ethyl acetate and dried to obtain 240.8 g of the expected product melting at 92° C.

1. temperaturecooled to +10° C.
2. additionwere introduced
3. customto rise to 17° C
4. customat 0° C.
5. stirringThe mixture was stirred for 2 hours at +10° C.
6. waitto rise to ambient temperature for 16 hours
7. stirringwith slower stirring
8. customAfter decanting
9. washthe organic phase was washed with water
10. extractionthe wash water was extracted with ethyl acetate and methylene chloride
11. additionThe combined organic phases were diluted with methylene chloride
12. customdried
13. customwere expelled at 40° C. under reduced pressure
14. customThe residue was triturated in 1300 ml of ethyl acetate for one hour
15. customseparated
16. washwashed with ethyl acetate
17. customdried

ORD record

ord-638f223778ee479590ea575c71e078fd

Source dataset

uspto-grants-1990_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04904655