Diethylaminoethyl chloride → HCID 21487244, Verbindung

Reaktionsgleichung

[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Cl[CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25]>>[CH2:22]([N:23]([CH2:26][CH3:27])[CH2:24][CH2:25][O:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:21]

Komponenten

Edukt 3

HCID 13364Diethylaminoethyl chloride

HCID 24758Sodium hydride

HCID 866702,3-dihydro-3-hydroxy-2-phenyl-1H-isoindol-1-one

Produkt 1

HCID 21487244HCID 21487244, VerbindungAusbeute 105,3 %

Versuchsvorschrift

Following the procedure of Example 6 but starting with 3-hydroxy-2-phenyl-isoindolin-1-one (22.5 g.), sodium hydride (50% dispersion in mineral oil) (5.3 g.) and 1-chloro-2-diethylaminoethane (13.5 g.), 3-(2-diethylaminoethoxy)-2-phenyl-isoindolin-1-one (34 g.) is obtained in the form of an 85% pure oil. On treating this oil (28 g.) with fumaric acid (8.5 g.) in ethanol, 3-(2-diethylaminoethoxy)-2-phenyl-isoindolin-1-one hydrogen fumarate (27.6 g.), which melts at 146°-147°C., is obtained.