Water → Tolterodine

HRID 2180918

Reaction equation

HRID 2180918 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C@@H:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:9][CH2:10][N:11]([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:7]=1.C(O)(C(O)=O)C(O)C(O)=O.O.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C@@H:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:9][CH2:10][N:11]([CH:12]([CH3:14])[CH3:13])[CH:15]([CH3:16])[CH3:17])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 9847786(R)-2-(3-(Diisopropylamino)-1-phenylpropyl)-4-methylphenol 2,3-dihydroxysuccinate

Product 1

HCID 443879Tolterodine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tolterodine tartrate (2.1 g) is mixed with water (45 ml) and toluene (2.5 ml). Sodium carbonate (800 mg) is added to the slurry. Sodium hydroxide (2.0 N, 1.5 ml) is added. The mixture is extracted three times with toluene (3 ml), saving the organic phase. Anhydrous potassium carbonate is added to the organic phase dissolve the tolterodine tartate, giving the title compound in solution.

Workup

  1. extractionThe mixture is extracted three times with toluene (3 ml)
  2. additionAnhydrous potassium carbonate is added to the organic phase
  3. dissolutiondissolve the tolterodine tartate

Sources & evidence

ORD record
ord-be8988cf4f904dc38f475ce707f7c13f
Source dataset
uspto-grants-2005_05
Patent number
US06890920B2

Linked notes

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