Trichloroacetic Acid → Methyl 2-(3-chloropropoxy)indole-3-carboxylate

HRID 496845

Reaktionsgleichung

Reaktionsgleichung von HRID 496845
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.CN1CCN(C)CC1.ClN1C(=O)CCC1=O.[Cl:30][CH2:31][CH2:32][CH2:33][OH:34].ClC(Cl)(Cl)C(O)=O>ClCCl>[Cl:30][CH2:31][CH2:32][CH2:33][O:34][C:2]1[NH:1][C:9]2[C:4]([C:3]=1[C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:6]=[CH:7][CH:8]=2

Komponenten

7

Edukt 5

HCID 6421Trichloroacetic AcidHCID 78181,4-DimethylpiperazineHCID 123133-Chloro-1-propanolHCID 31398ChlorosuccinimideHCID 589098Methyl indole-3-carboxylate

Produkt 1

HCID 9816818Methyl 2-(3-chloropropoxy)indole-3-carboxylateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of methyl indole-3-carboxylate and dichloromethane is cooled to 0° C. 1,4-dimethylpiperazine (0.55 eq.) and N-chlorosuccinimide (1.1 eq) are added and the mixture left to stir for two hours to give a slurry containing the compound of formula (C) above. The resulting slurry is added to a solution of 3-chloropropanol (1.1 eq) and trichloroacetic acid (0.12 eq) in dichloromethane, maintaining the temperature below 0° C. The reaction mixture is left to stir for half an hour, then washed with 10% aqueous sodium carbonate, 0.5 M hydrochloric acid and water. The organic solution is dried over sodium sulphate, filtered and the solvent evaporated. Toluene is added and the mixture stirred at 0-5° C. for one hour. The product is then filtered, washed with toluene and dried to give the title product in 83% yield.

Aufarbeitung

  1. waitthe mixture left
  2. customto give a slurry
  3. temperaturemaintaining the temperature below 0° C
  4. waitThe reaction mixture is left
  5. stirringto stir for half an hour
  6. washwashed with 10% aqueous sodium carbonate, 0.5 M hydrochloric acid and water
  7. dry with materialThe organic solution is dried over sodium sulphate
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. additionToluene is added
  11. stirringthe mixture stirred at 0-5° C. for one hour
  12. filtrationThe product is then filtered
  13. washwashed with toluene
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a22556098eba400f8396a5a1c34c3d64
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06946565B2

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