Methanesulfonic Acid → Rasagiline mesylate

HRID 505968Notes

Reaction equation

HRID 505968 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]>>[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

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 3052776Rasagiline

Product 1

HCID 3052775Rasagiline mesylateYield 85.54%

Conditions

Temperature
22.5 °C

Procedure

The toluenic phase of step (a) was charged into a 250 mL round-bottomed flask placed in a water/ice bath and equipped with mechanical stirrer. 9.25 mL of methanesulfonic acid were added in about 10-15 minutes, while maintaining the temperature below 22° C. After the addition, the reaction mixture was stirred for an additional 1 hour at 20-25° C. The mixture was then filtered and the filter was washed twice with 10.4 mL of toluene. 41.12 g of wet crude product were obtained (29.64 g of dry crude, partial yield: 85.54%; 79.65% by HPLC).

Workup

  1. customplaced in a water/ice bath
  2. customequipped with mechanical stirrer
  3. temperaturewhile maintaining the temperature below 22° C
  4. additionAfter the addition
  5. filtrationThe mixture was then filtered
  6. washthe filter was washed twice with 10.4 mL of toluene

Sources & evidence

ORD record
ord-466eccf224fc4befbbe6f0e81e8ea035
Source dataset
uspto-grants-2010_08
Patent number
US07781616B2

Reaction notes

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