Dimethylamine → 3-dimethylamino-methyl-1H-indole-6-carboxylic acid methyl ester

HRID 1272246

Reaktionsgleichung

Reaktionsgleichung von HRID 1272246
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=[O:2].[CH3:16][NH:17][CH3:18].[BH4-].[Na+].[CH3:21]O>C(Cl)(Cl)Cl.[Cl-].[Na+].O>[NH3:5].[CH3:1][OH:2].[CH3:15][O:14][C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:3]([N:17]([CH3:18])[CH3:16])=[CH:4][N:5]2[CH3:21])=[CH:10][CH:9]=1)=[O:13]

Komponenten

8

Edukt 4

HCID 674DimethylamineHCID 887MethanolHCID 735867methyl 3-formyl-1H-indole-6-carboxylateHCID 4311764Sodium borohydride

Produkt 2

HCID 21705897Ammonia methanolAusbeute 20 %HCID 695164543-dimethylamino-methyl-1H-indole-6-carboxylic acid methyl esterAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A solution of methyl 3-formylindole-6-carboxylate (8.0 g, 39.3 mmol) in 270 ml methanol is treated with dimethylamine (40% aqueous; 267 ml, 2.56 mol) at ambient temperature. After 45 minutes, NaBH4 (4.45 g, 118.1 mmol) is added, and the resulting mixture is heated at 55° C. for 3 hours. The reaction mixture is allowed to cool then is diluted with CHCl3 (200 ml) and brine (150 ml). The organic layer is washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue is purified by flash chromatography (SiO2; 100% ethyl acetate then 20% 2M NH3/methanol in CHCl3) to give 9.07 g of 3-dimethylamino-methyl-1H-indole-6-carboxylic acid methyl ester (99%). Amine 61 is prepared from 3-dimethylaminomethyl-1H-indole-6-carboxylic acid methyl ester by essentially following the procedures detailed in Amine 49, 1st paragraph; and Amine 51, 3rd paragraph.

Aufarbeitung

  1. temperatureto cool
  2. washThe organic layer is washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue is purified by flash chromatography (SiO2

Quellen und Nachweise

ORD-Eintrag
ord-2595965355ff47e19b1d69e5f4a9dd03
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208505B2

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