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Nifedipine → N-Methylnifedipine

HRID 399373
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 399373
[CH3:1][C:2]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:4]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[N+:19]([O-:21])=[O:20])[C:3]=1[C:22]([O:24][CH3:25])=[O:23].[H-].[Na+].CI.[C:30](OCC)(=O)C>O1CCCC1.CC(CC(C)=O)C.CCCCCC>[CH3:1][C:2]1[N:7]([CH3:30])[C:6]([CH3:8])=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:4]([C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1[C:22]([O:24][CH3:25])=[O:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 4485NifedipineHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydride2×

Produkt 1

HCID 14817573N-Methylnifedipine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 7909Methyl Isobutyl Ketone
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
38 °C

Versuchsvorschrift

12 g of nifedipine was disclosed in 50 ml of tetrahydrofuran in a nitrogen atmosphere. 1.66 g of a sodium hydride/oil dispersion (60% NaH) was added under agitation. Following agitation for some time, 10 ml of methyl iodide was added, and the resulting mixture was agitated for 1 hour at 38° C. 200 ml of ethyl acetate was then added. The resulting organic layer was washed several times with water, and was then dehydrated with sodium sulfate. The sodium sulfate was filtered out, and the solvent was removed. The solid obtained was dissolved in 200 ml of MIBK, and hexane was added producing 8.9 g of N-methylnifedipine in the form of yellow crystals. This compound had a melting point of 184° to 187° C.; an infrared absorption spectrum of 1690 cm-1 ; C=O, 1524 cm-1 ; N--O), and a proton-NMR spectrum (solvent: CDCl3) of 2.5 (6 H, methyl), 3.3 (3H, N-methyl), 3.6 (6H, O-methyl), 5.7 (1H, C--H, 7.2-7.6 (4H, C--H in aromatic nucleus).

Aufarbeitung

  1. additionwas added
  2. washThe resulting organic layer was washed several times with water
  3. filtrationThe sodium sulfate was filtered out
  4. customthe solvent was removed
  5. customThe solid obtained

Quellen und Nachweise

ORD-Eintrag
ord-df6e601094554948acb93bc45d40cf8c
Quelldatensatz
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05820944

Notizen zur Reaktion

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