Reaktion #83890

Reaktionsgleichung

(E)-1-[3-[[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-butenyl]oxy]-4-benzyloxyphenyl]ethanone

hydrochloric acid

→

(E)-1-[3-[[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-butenyl]oxy]-4-hydroxyphenyl]-ethanone hydrochloride

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAt the end of reaction
2. 2
   Sonstigethe solvent was reduced to about 20 ml on a rotary evaporator
3. 3
   workup.ADDITIONThe solution was poured into ice water (350 ml)
4. 4
   Extraktionextracted with dichloromethane (3×250 ml)
5. 5
   WaschenThe dichloromethane solution was washed with brine
6. 6
   Trocknendried over Na2SO4
7. 7
   SonstigeA solid formed on concentration of the solvent
8. 8
   FiltrationThis was collected by filtration (3.4 g)
9. 9
   SonstigeRecrystallization from hot methanol (40 ml)

Vorschrift

The mixture of (E)-1-[3-[[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-butenyl]oxy]-4-benzyloxyphenyl]ethanone (5.5 g, 10.7 mmol), acetic acid (50 ml), and hydrochloric acid (6 ml) was heated at 75° C. for 2 hours. At the end of reaction, the solvent was reduced to about 20 ml on a rotary evaporator. The solution was poured into ice water (350 ml) and extracted with dichloromethane (3×250 ml). The dichloromethane solution was washed with brine and dried over Na2SO4. A solid formed on concentration of the solvent. This was collected by filtration (3.4 g). Recrystallization from hot methanol (40 ml) gave 1.82 g of (E)-1-[3-[[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-butenyl]oxy]-4-hydroxyphenyl]-ethanone hydrochloride as white crystals, 37.5%, m.p.=208°-210° C.

Quelle