Lorazepam → Lormetazepam

HRID 1463969

Reaction equation

HRID 1463969 reaction equation
[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

Participants

5

Reactant 3

HCID 3958LorazepamHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 13314LormetazepamYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a0cb6a10ebc74883a8efd991da88e91a
Source dataset
uspto-grants-1994_04
Patent number
US05302715

Linked notes

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