Sodium Hydroxide → Rotigotine

HRID 1916001Notes

Reaction equation

HRID 1916001 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.O>[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

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24243Trisodium PhosphateHCID 180335Rotigotine hydrochloride

Product 1

HCID 59227Rotigotine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2400 g Rotigotine hydrochloride were added to a solution of 272.8 g NaOH in 3488 g ethanol (96%). The resulting mixture was stirred for approximately 10 minutes. Then 379.2 g of sodium phosphate buffer solution (27.6 g Na2HPO4×2H2O) and 53.2 g NaH2PO4×2H2O in 298.5 g water) was added. Insoluble or precipitated solids were separated from the mixture by filtration. The filter was rinsed with 964 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 964 g ethanol (96%)

Sources & evidence

ORD record
ord-6484a823319b47daa3568ec699004b91
Source dataset
uspto-grants-2013_12
Patent number
US08617591B2

Reaction notes

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