Sodium Hydroxide → Ropivacaine

HRID 1727380Notes

Reaction equation

HRID 1727380 reaction equation
[CH3:1][CH2:2][CH2:3][N:4]1[C@H:9]([C:10]([NH:12][C:13]2[C:14]([CH3:20])=[CH:15][CH:16]=[CH:17][C:18]=2[CH3:19])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5]1.C(C(C(C([O-])=O)O)O)([O-])=O.[OH-].[Na+]>O>[CH3:1][CH2:2][CH2:3][N:4]1[C@H:9]([C:10]([NH:12][C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:20])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86594745Ropivacaine tartrate

Product 1

HCID 175805Ropivacaine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under stirring, 126 g of ropivacaine tartrate were dissolved in 200 ml of water. To the resulting solution was added a solution of sodium hydroxide 1N, adjusting the pH of the solution around 10. During the addition of the alkaline solution, occurs the precipitation of raw base ropivacaine. The solid is filtered, washed in about 100 ml of distilled water and taken to the stove for drying. MP=142°-145° C., m=70 g (η=85.9%), [α]D25=−74.6° (c=2, MeOH).

Workup

  1. additionDuring the addition of the alkaline solution
  2. customthe precipitation of raw base ropivacaine
  3. filtrationThe solid is filtered
  4. washwashed in about 100 ml of distilled water
  5. customfor drying

Sources & evidence

ORD record
ord-e83da9cca65c475bb40009238be5a5fe
Source dataset
uspto-grants-2009_02
Patent number
US07495105B2

Reaction notes

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