Trifluoroacetic acid → Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amine

HRID 1633683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633683
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][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(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:24]([N:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][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 2

HCID 6422Trifluoroacetic acidHCID 695141225-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 21966638Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.45 g (6.8 mmol) 5-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 5 ml CH2Cl2 were treated with 4 ml TFA at 0° C. The solution was stirred at RT for 0.5 h, and at 40° C. for 1 h. The solution was concentrated, and the residue was dissolved in ether, water. 2M NaOH was added and the inorganic phase was extracted with ether. The combined organic phases were washed with water and dried over Na2SO4 to yield 1.65 g (94%) Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amine as light yellow oil, MS: 259 (MH+).

Aufarbeitung

  1. waitat 40° C. for 1 h
  2. concentrationThe solution was concentrated
  3. dissolutionthe residue was dissolved in ether
  4. addition2M NaOH was added
  5. extractionthe inorganic phase was extracted with ether
  6. washThe combined organic phases were washed with water
  7. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-d11f134c5fd243f18d81704c0f844521
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503907B2

Notizen zur Reaktion

Wird geladen…