Ethyl Acetate → Lorazepam

HRID 1700798

Reaction equation

HRID 1700798 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(O)C.C(OCC)(=O)C>C1CCCCC1>[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

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 18318790HCID 18318790, compound

Product 1

HCID 3958LorazepamYield 97.2%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
60 °C

Procedure

Lorazepam ethanol solvate (100 g) was suspended in a 1:1 mixture of ethyl acetate and cyclohexane (800 ml). The suspension was heated to 60° C. for 1 hour with rapid stirring and then cooled to 15° C. The cooled suspension was filtered to recover the lorazepam crystals and the crystals were then washed with ethyl acetate (20 ml). The crystals were dried at 50° C. under 65 mm Hg vacuum for two hours to give crystalline lorazepam (85 g, 90%).

Workup

  1. temperaturecooled to 15° C
  2. filtrationThe cooled suspension was filtered
  3. customto recover the lorazepam crystals
  4. washthe crystals were then washed with ethyl acetate (20 ml)
  5. customThe crystals were dried at 50° C. under 65 mm Hg vacuum for two hours

Sources & evidence

ORD record
ord-e77446ecc1754bb68f2c2868bde4cd7e
Source dataset
uspto-grants-2002_02
Patent number
US06350870B2

Linked notes

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