Water → 2-[3-[3-(N,N-Dimethylaminomethyl)phenoxy]propyl]-1H-isoindole-1,3(2H)-dione

HRID 1493177

Reaktionsgleichung

Reaktionsgleichung von HRID 1493177
[H-].[Na+].[CH3:3][N:4]([CH2:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1)[CH3:5].Br[CH2:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].O>CN(C)C=O>[CH3:5][N:4]([CH2:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[O:13][CH2:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2[C:20](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]1=[O:28])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 328963-(Dimethylaminomethyl)phenol

Produkt 1

HCID 128106112-[3-[3-(N,N-Dimethylaminomethyl)phenoxy]propyl]-1H-isoindole-1,3(2H)-dioneAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 80% sodium hydride (2.2 g) and 3-(N,N-dimethylaminomethyl)phenol (6.95 g) in dry dimethylformamide was stirred at 5° for 2 hr. N-(3-Bromopropyl)phthalimide (12.2 g) was then added and after 16 hours the reaction was treated with water and extracted with ethyl acetate. Evaporation of the dried organic extracts gave the title compound as a yellow oil (13 g). TLC silica; ethyl acetate; Rf 0.35. m.p. (oxalate salt) 204°-207°.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customEvaporation of the dried organic extracts

Quellen und Nachweise

ORD-Eintrag
ord-1b60f871c8a44f09b682726f41a6fcf1
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05021429

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