Dimethylamine → 1-[3-(Dimethylamino)propyl]-indole-3-acetamide

HRID 368737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 368737
CS(CCC[C:8]1[NH:9][C:10]2[C:15]([C:16]=1[CH2:17][C:18]([NH2:20])=[O:19])=[CH:14][CH:13]=[CH:12][CH:11]=2)(=O)=O.[CH3:21][NH:22][CH3:23].CCOC(C)=O.O.[CH2:31]1[CH2:35]OC[CH2:32]1>[Cl-].[Na+].O>[CH3:21][N:22]([CH2:32][CH2:31][CH2:35][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]([CH2:17][C:18]([NH2:20])=[O:19])=[CH:8]1)[CH3:23]

Komponenten

7

Edukt 5

HCID 674DimethylamineHCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 131721357HCID 131721357, Verbindung

Produkt 1

HCID 108488841-[3-(Dimethylamino)propyl]-indole-3-acetamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A suspension of 1-(methanesulfonylpropyl-indole-3-acetamide (1.0 g, 3.20 mmol) in THF (15 mL) was treated with a 40% aqueous solution of dimethylamine (13.5 mL, 0.108 mole) and the resultant reaction solution was capped and stirred at room temperature for 18 hours. The reaction was worked up extractively using EtOAc (50 mL), water (2×50 mL) and brine (25 ml). The combined aqueous layers were back-extracted three times with EtOAc (3×25 mL) and the combined organic layer dried (MgSO4) and the solvent removed in vacuo to give 0.77 g (92%) of 1-(Dimethylaminopropyl)-indole-3-acetamide. NMR. MS (FD) m/z=259 (M+, 100%).

Aufarbeitung

  1. customthe resultant reaction solution
  2. customwas capped
  3. extractionThe combined aqueous layers were back-extracted three times with EtOAc (3×25 mL)
  4. dry with materialthe combined organic layer dried (MgSO4)
  5. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-71a0492889f24701803363d5edd0adda
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133452

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