Reaktion #83923

Reaktionsgleichung

6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole

3-dimethylaminopropyl chloride hydrochloride

K2CO3

fumaric acid

→

white crystals

Ausbeute 56.9%

1-(3-Dimethylaminopropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine difumarate

Ausbeute 56.9%

Lösungsmittel

acetonitrile

water

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe aqueous phase was separated
2. 2
   Sonstigeacetonitrile was removed at reduced pressure
3. 3
   ExtraktionThe residue was extracted into DCM
4. 4
   WaschenThe organic solution was washed with H2O and brine
5. 5
   Trocknendried with MgSO4
6. 6
   SonstigeThe solvent was removed
7. 7
   SonstigeThe crystals were collected (2.53 g), m.p.=192°-194° C
8. 8
   SonstigeRecrystallization from ethanol

Vorschrift

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.05 g, 13.8 mmol), 3-dimethylaminopropyl chloride hydrochloride (3.4 g, 21 mmol), K2CO3 (6.2 g, 45 mmol), tetrabutylammonium hydrogen sulfate (phase transfer catalyst, 1.5 g) in acetonitrile (100 ml) and water (50 ml) was heated at 60° C. overnight. The aqueous phase was separated, and acetonitrile was removed at reduced pressure. The residue was extracted into DCM. The organic solution was washed with H2O and brine, then dried with MgSO4. The solvent was removed and the crude product (4.3 g) was treated with fumaric acid (1.58 g, 1.0 eq) in dilute ethanol. The crystals were collected (2.53 g), m.p.=192°-194° C. Recrystallization from ethanol yielded 2.08 g of white crystals, mp=194°-195° C.

Quelle