Hydrochloric Acid → Fingolimod Hydrochloride
Reaction equation
[OH:1][CH2:2][C:3]([NH:22]C(=O)C)([CH2:20][OH:21])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:8][CH:7]=1.[ClH:26]>>[CH3:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([NH2:22])([CH2:2][OH:1])[CH2:20][OH:21])=[CH:7][CH:8]=1.[ClH:26]Participants
3
Conditions
- Temperature
- 100 °C
Procedure
N-(1-Hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl)butan-2-yl) acetamide (23.5 g) is charged into a 250 mL single-neck round bottom flask equipped with a condenser and 3N hydrochloric acid (100 mL) is added. The mixture is heated to 100° C. and stirred for 3 hours. The mass is cooled to room temperature and maintained overnight. The mass is extracted with ethyl acetate (3×100 mL) and the ethyl acetate extracts are combined, dried with sodium sulphate, and concentrated under vacuum to produce a gummy solid. Ethanolic hydrochloride solution is added to the solid, stirred for 3 hours at room temperature and the obtained solid is separated by filtration and suction dried. The solid is recrystallized from an isopropyl alcohol solution to give fingolimod hydrochloride. Yield: 5.7 g.