Lorazepam → Lormetazepam

HRID 1463969

Reaktionsgleichung

Reaktionsgleichung von HRID 1463969
[CH:1]1[CH:2]=[CH:3][C:4]([Cl:21])=[C:5]([C:7]2[C:14]3[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=3[NH:12][C:10](=[O:11])[CH:9]([OH:20])[N:8]=2)[CH:6]=1.[C:22](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:22][N:12]1[C:10](=[O:11])[CH:9]([OH:20])[N:8]=[C:7]([C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=2[Cl:21])[C:14]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]1=2

Komponenten

5

Edukt 3

HCID 3958LorazepamHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Produkt 1

HCID 13314LormetazepamAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirring solution of lorazepam (3.21 g, 1.0×10-2 mol) in anhydrous dimethylformamide (100 ml) was added anhydrous powdered potassium carbonate (1.52 g, 1.1×10-2 mol) followed by iodomethane (0.69 ml, 1.1×10-2 mol). The mixture was stirred at room temperature for 20 hours. The solvent was evaporated under vacuum, the residue was treated with water (100 ml) and was stirred at room temperature for 2 hours. The resulting fine light yellow solid was collected by filtration and was dried under vacuum to afford 3.3 g (98%) of lormetazepam as a pale yellow solid: m.p. 201°-203° C.

Aufarbeitung

  1. customThe solvent was evaporated under vacuum
  2. additionthe residue was treated with water (100 ml)
  3. stirringwas stirred at room temperature for 2 hours
  4. filtrationThe resulting fine light yellow solid was collected by filtration
  5. customwas dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a0cb6a10ebc74883a8efd991da88e91a
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05302715

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