Dimethyl(methylene)ammounium iodide → 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide

HRID 8122

Reaktionsgleichung

Reaktionsgleichung von HRID 8122
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[CH3:14][N+:15]([CH3:17])=[CH2:16].[I-:18]>C(O)(=O)C>[IH:18].[CH3:13][O:12][C:10]([C:5]1[C:4]2[C:3]([CH2:14][N:15]([CH3:17])[CH3:16])=[CH:2][NH:1][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:11]

Komponenten

4

Edukt 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 2733668methyl 1H-indole-4-carboxylate

Produkt 1

HCID 695180113-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Methyl indole-4-carboxylate (7.0 g, 40 mmol) and Eschenmoser's salt (N,N-dimethylmethyleneammonium iodide; 7.8 g, 42 mmol) are combined in 130 ml of acetic acid. After heating at 65° C. for 2 hours, the reaction mixture is concentrated in vacuo. The resulting solid is triturated with ethyl acetate, filtered and dried in vacuo to give 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide in quantitative yield.

Aufarbeitung

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. customThe resulting solid is triturated with ethyl acetate
  3. filtrationfiltered
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c7d2f163f53541348b1ec62b194c7f1c
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087635B2

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