Hydrochloric Acid → Fingolimod Hydrochloride

HRID 2172652Notes

Reaction equation

HRID 2172652 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

17.0 gm of fingolimod was dissolved in (1:1) ethanol 120 ml:IPE.HCl 120 ml solutions. The reaction mass was stirred for about 30 min at room temperature; then concentrated under vacuum at about 40-45° C. 51 ml ethanol was added. The reaction mass was heated to about 50-55° C. and 200 ml ethyl acetate was added into the reaction mass. The reaction mass was cooled to about 5-10° C. and stirred for about 30 min. The solid obtained was filtered and washed with ethyl acetate to get 14.6 g of compound of Fingolimod hydrochloride. Purity 99.75% and regioisomer impurity compound of Formula IA: 0.006% by HPLC.

Workup

  1. concentrationthen concentrated under vacuum at about 40-45° C
  2. addition51 ml ethanol was added
  3. temperatureThe reaction mass was heated to about 50-55° C.
  4. addition200 ml ethyl acetate was added into the reaction mass
  5. temperatureThe reaction mass was cooled to about 5-10° C.
  6. stirringstirred for about 30 min
  7. customThe solid obtained
  8. filtrationwas filtered
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-da77f5c302fa4245ab7f5d56ac0798f0
Source dataset
uspto-grants-2015_06
Patent number
US09056813B2

Reaction notes

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