Hydrochloric Acid → [5-(2-methoxy-ethoxy)-1H-indol-ylmethyl]-dimethyl-amine

HRID 41060

Reaktionsgleichung

Reaktionsgleichung von HRID 41060
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.[CH2:15]=O.Cl.[CH3:18][NH:19][CH3:20]>C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:18][N:19]([CH3:15])[CH3:20])[CH:10]=[CH:9]2

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 103525375-(2-methoxyethoxy)-1H-indole

Produkt 1

HCID 66938466[5-(2-methoxy-ethoxy)-1H-indol-ylmethyl]-dimethyl-amineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 5-(2-methoxy-ethoxy)-indole (2.06 g, 11.0 mmol) in acetic acid (7 ml) and 40% aqueous dimethylamine (2.1 ml) is cooled to 0° C., and 36% aqueous formaldehyde (1.38 ml) (pre-cooled to 0° C.) is added drop wise. The mixture is stirred at room temperature overnight, 2 M hydrochloric acid is added, and the mixture is washed with dichloromethane. The aqueous layer is made alkaline with 10% NaOH, and is extracted with dichloromethane. The combined organic layer is washed with water, is dried and concentrated. The residue is purified by column chromatography (dichloromethane-methanol, 4:1→dichloromethane-methanol-water-aqueous ammonia, 10:20:1:1) to afford [5-(2-methoxy-ethoxy)-1H-indol-ylmethyl]-dimethyl-amine (2.42 g, 90%). M.p. 163-164° C. (from toluene-N,N-dimethylformamide).

Aufarbeitung

  1. washthe mixture is washed with dichloromethane
  2. extractionis extracted with dichloromethane
  3. washThe combined organic layer is washed with water
  4. customis dried
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography (dichloromethane-methanol, 4:1→dichloromethane-methanol-water-aqueous ammonia, 10:20:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-647412664e524dd98d16f3f196ff2ed6
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530493B2

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