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

HRID 2221283

Reaktionsgleichung

Reaktionsgleichung von HRID 2221283
[CH3:1][NH:2][CH3:3].[CH2:4]=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2>C(O)(=O)C>[Br:6][C:7]1[CH:8]=[C:9]2[C:3](=[CH:14][CH:15]=1)[NH:2][CH:1]=[C:10]2[CH2:11][N:12]([CH3:4])[CH3:13]

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 249055-Bromoindole

Produkt 1

HCID 13249Indole, 5-bromo-3-(dimethylamino)methyl-Ausbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a mixture of 40% aqueous dimethylamine (5.95 g, 52.8 mmol), 37% aqueous formaldehyde (4.21 g, 51.9 mmol) and acetic acid (7 mL) was added 5-bromo-1H-indole (9.79 g, 49.9 mmol). The reaction mixture was stirred for 21 hours at room temperature and poured into a 2.5 N sodium hydroxide/ice mixture (200 mL). This was extracted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated to dryness. It was dried at 60° C. for 30 minutes to yield (5-bromo-1H-indol-3-ylmethyl)-dimethyl-amine (11.2 g) as a brown solid: mp 160-162° C. 1HNMR (200 MHz, DMSO-d6): δ 11.1 (br s, 1H), 7.75 (s, 1H), 7.15-7.35 (m, 3H), and 3.5 ppm (s, 2H).

Aufarbeitung

  1. extractionThis was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customIt was dried at 60° C. for 30 minutes

Quellen und Nachweise

ORD-Eintrag
ord-7d2f38c42fcb43f2a2f138504754a1da
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368471B2

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