Zolpidem → Zolpidem methanesulfonate

HRID 1066185Notes

Reaction equation

HRID 1066185 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]=[C:15]3[N:10]([CH:11]=[C:12]([CH3:17])[CH:13]=[CH:14]3)[C:9]=2[CH2:18][C:19]([N:21]([CH3:23])[CH3:22])=[O:20])=[CH:6][CH:7]=1.[CH3:24][S:25]([OH:28])(=[O:27])=[O:26]>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]=[C:15]3[N:10]([CH:11]=[C:12]([CH3:17])[CH:13]=[CH:14]3)[C:9]=2[CH2:18][C:19]([N:21]([CH3:22])[CH3:23])=[O:20])=[CH:4][CH:3]=1.[CH3:24][S:25]([O-:28])(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 5732ZolpidemHCID 6395Methanesulfonic Acid

Product 1

HCID 18004025Zolpidem methanesulfonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

One gram of zolpidem free base is dissolved in 10 ml of ethanol at 50° C. Then 0.313 g (a molar equivalent) of methane sulfonic acid is added at this temperature, the mixture is stirred for 5 minutes and evaporated to dryness under reduced pressure. The residue is treated with 10 ml of acetone, the remaining solid is filtered off and washed with 5 ml of acetone and dried in vacuum oven at 40° C. to yield zolpidem methanesulfonate. A representative DSC curve is shown in FIG. 12.

Workup

  1. customevaporated to dryness under reduced pressure
  2. additionThe residue is treated with 10 ml of acetone
  3. filtrationthe remaining solid is filtered off
  4. washwashed with 5 ml of acetone
  5. customdried in vacuum oven at 40° C.

Sources & evidence

ORD record
ord-7de80f1e39ee48d580eb39c9d7b667d9
Source dataset
uspto-grants-2001_06
Patent number
US06242460B1

Reaction notes

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