Hydrochloric Acid → Fingolimod Hydrochloride

HRID 1505009Notes

Reaction equation

HRID 1505009 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([NH2:22])([CH2:20][OH:21])[CH2:18][OH:19])=[CH:13][CH:14]=1.[ClH:23]>C(O)C>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH2:22])([CH2:18][OH:19])[CH2:20][OH:21])=[CH:11][CH:10]=1.[ClH:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 107970Fingolimod

Product 1

HCID 107969Fingolimod Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In an embodiment, fingolimod hydrochloride may be obtained by dissolving fingolimod of step b) in ethanol, cooling the reaction mixture to 0° C. to 5° C., adding ethanolic hydrochloride solution drop wise over a period of 10 to 30 minutes at the same temperature to obtain a suspension, maintaining the suspension at the same temperature for 1 to 3 hours, filtering the obtain solid, washing with an ether solvent and optionally drying the product obtained to give fingolimod hydrochloride.

Workup

  1. temperaturecooling the reaction mixture to 0° C. to 5° C.
  2. customto obtain a suspension
  3. temperaturemaintaining the suspension at the same temperature for 1 to 3 hours
  4. filtrationfiltering the obtain solid
  5. washwashing with an ether solvent
  6. customoptionally drying the product
  7. customobtained

Sources & evidence

ORD record
ord-25957b60a1c045bc81780e54440473fd
Source dataset
uspto-grants-2015_12
Patent number
US09216943B2

Reaction notes

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