Sodium Iodide → N-benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine

HRID 447749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 447749
Cl[CH2:2][CH2:3][CH:4]1[CH2:12][CH2:11][CH2:10][C:9]2[N:8]([CH3:13])[CH:7]=[CH:6][C:5]1=2.[CH3:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[CH2:16]([N:15]([CH3:14])[CH2:2][CH2:3][CH:4]1[CH2:12][CH2:11][CH2:10][C:9]2[N:8]([CH3:13])[CH:7]=[CH:6][C:5]1=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 7669N-MethylbenzylamineHCID 11430Potassium CarbonateHCID 690791294-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole

Produkt 1

HCID 17751624N-benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamineAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole (0.1 g, 0.5 mmol), N-methyl-N-benzylamine (0.07 g, 0.5 mmol), K2CO3 (0.20 g, 1.45 mmol) and a catalytic amount of NaI in DMF (5 mL) is heated to 110° C. overnight. The solvent is removed at reduced pressure, diethyl ether is added to the residue and washed with water. The organic phase is dried and evaporated at reduced pressure and the resulting crude is purified by column chromatography, giving N-benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine (0.04 g, 0.14 mmol, 28%, oil). (ESI-MS m/z 283 (M+H)+.

Aufarbeitung

  1. customThe solvent is removed at reduced pressure, diethyl ether
  2. additionis added to the residue
  3. washwashed with water
  4. customThe organic phase is dried
  5. customevaporated at reduced pressure
  6. customthe resulting crude is purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cb149c94882848bd882c1aa86324c406
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481567B2

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