Toluene → Rasagiline

HRID 1986154Notes

Reaction equation

HRID 1986154 reaction equation
CS(O)(=O)=O.[CH:6]#[C:7][CH2:8][NH:9][C@H:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11]1.C1(C)C=CC=CC=1.[OH-].[Na+]>O>[CH:6]#[C:7][CH2:8][NH:9][C@H:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 3052775Rasagiline mesylate

Product 1

HCID 3052776Rasagiline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

120 g of rasagiline mesylate (R(+)-N-propargyl-1-aminoindan mesylate) were dissolved in 700 ml of deionized water. 400 ml of toluene were added and the mixture was basified with 25% NaOH solution to a pH of about 14. After stirring, two phases separated. The lower water phase was extracted with 200 ml of toluene. The phases were allowed to separate and the aqueous phase was discarded.

Workup

  1. customtwo phases separated
  2. extractionThe lower water phase was extracted with 200 ml of toluene
  3. customto separate

Sources & evidence

ORD record
ord-6110342d560d4da6b9ef34a9ff8a38b7
Source dataset
uspto-grants-2009_06
Patent number
US07547806B2

Reaction notes

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