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Sodium Hydroxide → 2-((2-(1H-Indol-3-yl)ethyl)amino)ethanol

HRID 1199937
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HRID 1199937 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][CH2:13][C:14](OCC)=[O:15])=[CH:2]1.[OH-].[Na+]>O1CCCC1.C1(C)C=CC=CC=1.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][CH2:13][CH2:14][OH:15])=[CH:2]1
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참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 14477069HCID 14477069, 화합물

생성물 1

HCID 123571312-((2-(1H-Indol-3-yl)ethyl)amino)ethanol수율 73%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

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온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-638f223778ee479590ea575c71e078fd
출처 데이터셋
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04904655

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