N-Methylethylenediamine → (1-Methyl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester

HRID 48321

Reaktionsgleichung

[CH2:1]([O:3][P:4]([CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1F)=O)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[CH3:19][NH:20][CH2:21][CH2:22][NH2:23]>N1C=CC=CC=1>[CH2:1]([O:3][P:4]([CH:9]=[C:10]1[NH:23][CH2:22][CH2:21][N:20]([CH3:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]1=2)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

A mixture of 10.45 g (38.1 mmol) of [2-(2-fluorophenyl)-2-oxoethyl]phosphonic acid diethyl ester and 14.1 g (190 mmol) N-methylethylenediamine in 100 ml of pyridine was heated at 95° C. for 18 hours. The solvent was evaporated and the residue was partitioned between 200 ml of water and 2×100 ml of dichloromethane. The combined organic portions were dried (magnesium sulphate), filtered and evaporated. The residue was purified by column chromatography eluting with 5% methanol/dichloromethane to give 3.14 g (26%) of (1-methyl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester as a light brown oil; MS: m/e 311.0 [M+H]+.

Aufarbeitung

customThe solvent was evaporated
customthe residue was partitioned between 200 ml of water and 2×100 ml of dichloromethane
dry with materialThe combined organic portions were dried (magnesium sulphate)
filtrationfiltered
customevaporated
customThe residue was purified by column chromatography
washeluting with 5% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag: ord-deca01e94d734623854fc9a21f58b731
Quelldatensatz: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06703387B2

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