2,3-Epoxypropyl 4'-methoxyphenyl ether → Dimethyl 4-[2-[4-[2-hydroxy-3-(p-methoxyphenoxy)propylamino]butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 4666

Reaktionsgleichung

Reaktionsgleichung von HRID 4666
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[CH:16]1[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:26])[NH:19][C:18]([CH3:27])=[C:17]1[C:28]([O:30][CH3:31])=[O:29].[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH:42]2[O:44][CH2:43]2)=[CH:36][CH:35]=1>CO>[OH:44][CH:42]([CH2:41][O:40][C:37]1[CH:38]=[CH:39][C:34]([O:33][CH3:32])=[CH:35][CH:36]=1)[CH2:43][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[CH:16]1[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:26])[NH:19][C:18]([CH3:27])=[C:17]1[C:28]([O:30][CH3:31])=[O:29]

Komponenten

4

Edukt 2

HCID 166462,3-Epoxypropyl 4'-methoxyphenyl etherHCID 14306630Dimethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Produkt 1

HCID 14050462Dimethyl 4-[2-[4-[2-hydroxy-3-(p-methoxyphenoxy)propylamino]butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In 200 ml of methanol were dissolved 2 g of dimethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 0.84 g of glycidyl 4-methoxyphenyl ether, and the solution was refluxed under heating for 3 hours. The solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography, and the product was eluted with chloroform-methanol (95:5 v/v). Crude crystals were recrystallized from a mixture of methanol and ethyl ether to give 0.85 g of dimethyl 4-[2-[4-[2-hydroxy-3-(p-methoxyphenoxy)propylamino]butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate.

Aufarbeitung

  1. temperaturethe solution was refluxed
  2. temperatureunder heating for 3 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. washthe product was eluted with chloroform-methanol (95:5 v/v)
  5. customCrude crystals were recrystallized from a mixture of methanol and ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-065611ec619f447a9db829eeb34ff8e9
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727082

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