Trifluoroacetic acid → 1-Methyl-1H-indole-3-ethylamine

HRID 1749513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749513
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][NH:13]C(=O)OC(C)(C)C)=[CH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][NH2:13])=[CH:3]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71202127Tert-butyl N-[2-(1-methyl-1H-indol-3-YL)ethyl]carbamate

Produkt 1

HCID 234921-Methyl-1H-indole-3-ethylamineAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butyl (2-(1-methyl-1H-indol-3-yl)ethyl)carbamate (1.29 g, 4.71 mmol) in DCM (15 mL) was added TFA (7 mL) at ˜0° C. to 5° C. The resulting reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated to give the crude product which was diluted with DCM and washed with sodium bicarbonate aqueous solution. The organic layer was washed with brine, dried and concentrated to give the desired product (700 mg, 4.02 mmol, 85% yield) as yellow oil. MS (ESI) m/z 175.1 [M+H]+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. customto give the crude product which
  4. washwashed with sodium bicarbonate aqueous solution
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5faad02c97c942e18f1d277cdf32f2f7
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156798B2

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