Methanesulfonic Acid → Rasagiline mesylate

HRID 401853Notes

Reaction equation

HRID 401853 reaction equation
[CH:1]#[C:2][CH2:3][NH:4][C@H:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6]1.[CH3:14][S:15]([OH:18])(=[O:17])=[O:16]>CC(O)C>[CH3:14][S:15]([OH:18])(=[O:17])=[O:16].[CH:1]#[C:2][CH2:3][NH:4][C@H:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 3052776Rasagiline

Product 1

HCID 3052775Rasagiline mesylateYield 83.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
5 °C

Procedure

Rasagiline base (81 g, 0.47 moles) was dissolved in IPA (810 ml) under stirring and the obtained solution was cooled to 5° C. A solution of methanesulfonic acid (0.49 moles, 47.7 g) in IPA (95 ml) was added dropwise to the above cooled solution. After complete addition, the mixture was stirred for 30 min at 5-10° C. to get the solid which was filtered and dried to get (105 g, 83%) of Rasagiline mesylate.

Workup

  1. additionAfter complete addition
  2. stirringthe mixture was stirred for 30 min at 5-10° C.
  3. customto get the solid which
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-3ba668adc1934c91ba8d932d1597670e
Source dataset
uspto-grants-2014_06
Patent number
US08741962B2

Reaction notes

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