N,N-Dimethylaniline → Benzyl 4-(2-oxo-1-pyrrolidinyl)phenylcarbamate

HRID 499733

Reaktionsgleichung

Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=[O:24])=[CH:15][CH:14]=1.CN(C)C1C=CC=CC=1.C(OCC)(=O)C>O1CCCC1>[O:24]=[C:20]1[CH2:21][CH2:22][CH2:23][N:19]1[C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:2](=[O:3])[O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:14][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: -20 °C

Versuchsvorschrift

4.27 g (25.03 mmol) of benzyl chloroformate are slowly added to 4 g (22.7 mmol) of 1-(4-aminophenyl)pyrrolidin-2-one and 3.6 ml (28.4 mmol) of N,N-dimethylaniline in 107 ml of tetrahydrofuran at −20° C. The mixture is stirred at −20° C. for 30 minutes and then allowed to reach room temperature. 0.5 l of ethyl acetate is added, and the organic phase is washed with 0.5 l of saturated NaCl solution. The removed organic phase is dried with MgSO4, and the solvent is evaporated in vacuo. The residue is triturated with diethyl ether and filtered off with suction. 5.2 g (73.8% of theory) of benzyl 4-(2-oxo-1-pyrrolidinyl)phenylcarbamate are obtained as pale beige crystals with a melting point of 174° C.

Aufarbeitung

customto reach room temperature
washthe organic phase is washed with 0.5 l of saturated NaCl solution
dry with materialThe removed organic phase is dried with MgSO4
customthe solvent is evaporated in vacuo
customThe residue is triturated with diethyl ether
filtrationfiltered off with suction

Quellen und Nachweise

ORD-Eintrag: ord-b678ad7d47524d1ab57465d1e6ea7d61
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07767702B2

Verknüpfte Notizen

Wird geladen…