Dimethylamine → Indole, 5-bromo-3-(dimethylamino)methyl-

HRID 330277

Reaktionsgleichung

Reaktionsgleichung von HRID 330277
[CH2:1]=O.[CH3:3][NH:4][CH3:5].O.[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2>O1CCOCC1>[Br:7][C:8]1[CH:9]=[C:10]2[C:5](=[CH:15][CH:16]=1)[NH:4][CH:3]=[C:11]2[CH2:12][N:13]([CH3:1])[CH3:14]

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 962WaterHCID 249055-Bromoindole

Produkt 1

HCID 13249Indole, 5-bromo-3-(dimethylamino)methyl-Ausbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

According to A. Ek, et al., J Am. Chem. Soc., 76, 5579 (1954), to an ice-cooled mixture of dioxane (130 mL) acetic acid (130 mL) , 37% aqueous formaldehyde (9.9 mL, 0.133 mol), 40% aqueous dimethylamine (17.6 mL, 0.140 mol), and H2O (10.6 mL) was added a solution of 5-bromoindole (25.0 g, 0.128 mol) in dioxane (130 mL) over 35 minutes. The internal temperature was maintained at 5° C. during the addition. After 2 hours, the cooling bath was removed and stirring was continued at room temperature overnight. The mixture was diluted with H2O (1600 mL), charcoal and celite were added and the mixture was filtered. 2.5 N NaOH (1000 mL) was added and the resulting precipitate was collected by filtration to yield 98% of product as a white solid.

Aufarbeitung

  1. customthe cooling bath was removed
  2. waitwas continued at room temperature overnight
  3. additionThe mixture was diluted with H2O (1600 mL), charcoal and celite
  4. additionwere added
  5. filtrationthe mixture was filtered
  6. addition2.5 N NaOH (1000 mL) was added
  7. filtrationthe resulting precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-a5947a28d4e94a49948e1b5ae2bf71f0
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04895860

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