Sodium Hydroxide → Rotigotine

HRID 1916002Notes

Reaction equation

HRID 1916002 reaction equation
[CH3:1][CH2:2][CH2:3][N:4]([C@@H:12]1[CH2:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:21]([OH:22])[C:15]=2[CH2:14][CH2:13]1)[CH2:5][CH2:6][C:7]1[S:11][CH:10]=[CH:9][CH:8]=1.Cl.[OH-].[Na+].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>C(O)C>[CH3:1][CH2:2][CH2:3][N:4]([C@@H:12]1[CH2:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:21]([OH:22])[C:15]=2[CH2:14][CH2:13]1)[CH2:5][CH2:6][C:7]1[S:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24243Trisodium PhosphateHCID 180335Rotigotine hydrochloride

Product 1

HCID 59227Rotigotine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

150 g Rotigotine hydrochloride were added to a solution of 17.05 g NaOH in 218 g ethanol (96%). The resulting mixture was stirred for approximately 10 minutes. Then 23.7 g of sodium phosphate buffer solution (8.35 g Na2HPO4×2H2O and 16.07 g NaH2PO4×2H2O in 90.3 g water) was added. Insoluble or precipitated solids were separated from the mixture by filtration. The filter was rinsed with 60.4 g ethanol (96%) to obtain a particle-free ethanolic solution of rotigotine essentially in the form of the free base.

Workup

  1. customInsoluble or precipitated solids
  2. customwere separated from the mixture by filtration
  3. washThe filter was rinsed with 60.4 g ethanol (96%)

Sources & evidence

ORD record
ord-37a6a86f39714b989c258fa1e8fdfad9
Source dataset
uspto-grants-2013_12
Patent number
US08617591B2

Reaction notes

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