5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester → Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amine

HRID 1633677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633677
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:24][CH:25]=[CH2:26])[CH3:23])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:24]([N:22]([CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][CH2:9][CH2:10]2)[CH3:23])[CH:25]=[CH2:26]

Komponenten

4

Edukt 1

HCID 695147375-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 21966572Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amineAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To 7.3 g (20.2) 5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 15 ml CH2Cl2, 10 ml trifluoro acetic acid were added at 0° C. The mixture was stirred at reflux for 3 h and was concentrated in vacuo. Water and 2M NaOH were added and the inorganic phase was extracted with ether. The combined organic phases were washed with water and dried over Na2SO4. Evaporation yielded 5.2 g (98%) Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amine as orange oil, MS: 261 (MH+)

Aufarbeitung

  1. temperatureat reflux for 3 h
  2. concentrationwas concentrated in vacuo
  3. additionWater and 2M NaOH were added
  4. extractionthe inorganic phase was extracted with ether
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-52b837f5bacd4dc9ab6ae46e5aa51e1b
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503907B2

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