Dextromethorphan hydrobromide monohydrate → Dextromethorphan

HRID 1244212Notes

Reaction equation

HRID 1244212 reaction equation
[CH3:1][N:2]1[C@H:11]2[CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[C@:5]3([C@@H:10]2[CH2:9][CH2:8][CH2:7][CH2:6]3)[CH2:4][CH2:3]1.O.Br>C(#N)C.[N+]([O-])([O-])=O.[Ag+]>[CH3:1][N:2]1[C@H:11]2[CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[C@:5]3([C@@H:10]2[CH2:9][CH2:8][CH2:7][CH2:6]3)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 5462351Dextromethorphan hydrobromide monohydrate

Product 1

HCID 5360696Dextromethorphan

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6342AcetonitrileSolvent

Procedure

The salt is prepared by adding silver nitrate (0.96 g, 5.68 mmoles) to a solution of Dextromethorphan hydrobromide (2 g, 5.68 mmoles) in acetonitrile (20 ml). The solution is then stirred at room temperature for 30 minutes. Filtering is then effected to remove silver bromide precipitate. The clear solution is added of ethyl ether (110 ml). A precipitate is formed, that is filtered, washed with ethyl ether and dried under vacuum. The solid obtained at the elemental analysis corresponds to the nitrate salt of Dextromethorphan:

Workup

  1. customThe salt is prepared
  2. filtrationFiltering
  3. customto remove silver bromide precipitate
  4. additionThe clear solution is added of ethyl ether (110 ml)
  5. customA precipitate is formed
  6. filtrationthat is filtered
  7. washwashed with ethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-476de4ffc15842f9971d177722be1024
Source dataset
uspto-grants-2006_10
Patent number
US07122539B2

Reaction notes

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