Flordipine → Diethyl 1,4-dihydro-2,6-dimethyl-1-[2-(4-morpholinyl)ethyl]-4-[2-(trifluoromethyl)phenyl]-3,5-pyridinedicarboxylate maleate

HRID 2164321

Reaktionsgleichung

Reaktionsgleichung von HRID 2164321
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:9][C:10]1[N:11]([CH2:37][CH2:38][N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[C:12]([CH3:36])=[C:13]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CC(C)=O.CCOC(C)=O>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:36][C:12]1[N:11]([CH2:37][CH2:38][N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[C:10]([CH3:9])=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:28])[F:29])[C:13]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Komponenten

5

Edukt 2

HCID 53699FlordipineHCID 444266Maleic Acid

Produkt 1

HCID 70486598Diethyl 1,4-dihydro-2,6-dimethyl-1-[2-(4-morpholinyl)ethyl]-4-[2-(trifluoromethyl)phenyl]-3,5-pyridinedicarboxylate maleateAusbeute 107 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1.2 g of maleic acid in 12 ml of acetone was added to a solution of 5.1 g of diethyl 1,4-dihydro-2,6-dimethyl-1-[2-(4-morpholinyl)ethyl]-4-[2-(trifluoromethyl)phenyl]-3,5-pyridinedicarboxylate in 50 ml of EtOAc. The reaction mixture was refluxed and filtered hot to yield 6.7 g of diethyl 1,4-dihydro-2,6-dimethyl-1-[2-(4-morpholinyl)ethyl]-4-[2-(trifluoromethyl)phenyl]-3,5-pyridinedicarboxylate maleate. This was partitioned between 5 parts of toluene and 10 parts of 10% NaOH, the toluene phase was dried over anhydrous Na2SO4, and dilution with 10 parts of heptane yielded 3.9 g (76%) of diethyl 1,4-dihydro-2,6-dimethyl-1-[2-(4-morpholinyl)ethyl]-4-[2-(trifluoromethyl)phenyl]-3,5-pyridinecarboxylate. Analysis by analytical HPLC indicated the presence of 0.17% of ##STR12##

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed
  2. filtrationfiltered hot

Quellen und Nachweise

ORD-Eintrag
ord-712c7d6bf430457ca60ac37a3f960135
Quelldatensatz
uspto-grants-1985_03
Patentnummer
US04503223

Verknüpfte Notizen

Wird geladen…