Dimethylformamide → (+/-)-1-[(4-Chlorobenzyl)morpholin-2-yl]-2-(2-methoxyphenyl)-ethene oxalic acid salt

HRID 1532994

Reaktionsgleichung

[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][NH:7][CH2:8]C[OH:10])=[CH:4][CH:3]=1.[C:13]([O:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][O:21][C:22](=O)[CH3:23])(=[O:15])C.C(N(CC)CC)C.I[C:33]1[CH:38]=[CH:37][CH:36]=C[C:34]=1[O:39][CH3:40].C(N(C(C)C)CC)(C)C.CN([CH:53]=[O:54])C>C1COCC1.CCOCC>[C:53]([OH:54])(=[O:10])[C:13]([OH:16])=[O:15].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:23][CH2:22][O:21][CH:20]([CH:19]=[CH:18][C:17]3[CH:36]=[CH:37][CH:38]=[CH:33][C:34]=3[O:39][CH3:40])[CH2:8]2)=[CH:11][CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

A mixture of N-(4-chlorobenzyl)-N-(2-hydroxyethyl) amine (2.00 g, 10.8 mmol) and cis-1,4-diacetoxy-2-buten (2.78 g, 16.2 mmol), triethylamine (3.26 g, 32.3 mmol), tetrakis triphenylphosphino palladium(O) (0.31 g, 0.27 mmol) in THF (20 ml) was refluxed overnight. DMF (10 ml) was added and the THF was stripped off in vacuum. Addition of 2-iodoanisole (3.8 g, 16.2 mmol) and diisopropylethylamine (2.8 g, 21.6 mmol) was followed by heating to 130° C. overnight. Ether was added and the organics were washed twice with aqueous sodium hydroxide (1 M). Chromatography on silica gel with dichloromethane with 1% methanol as the eluent gave the free base. Dissolution in ether and precipitation with oxalic acid gave the title compound. Yield 1.0 g, 21%. mp 178-180° C.

Aufarbeitung

temperaturewas refluxed overnight
washthe organics were washed twice with aqueous sodium hydroxide (1 M)
customChromatography on silica gel with dichloromethane with 1% methanol as the eluent gave the free base
customprecipitation with oxalic acid

Quellen und Nachweise

ORD-Eintrag: ord-5f20e29e5b034c86b77ca0e8bd73a0a0
Quelldatensatz: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06207662B1

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