Acetonitrile → 3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)propan-1-ol

HRID 235407

Reaktionsgleichung

Reaktionsgleichung von HRID 235407
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH2:26][OH:27].C(#N)C>O>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:24][CH2:25][CH2:26][OH:27])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Produkt 1

HCID 153849663-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)propan-1-olAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (10.0 g, 45 mmol), K2CO3 (10.0 g), 3-bromo-1-propanol (7.3 g, 46 mmol) and acetonitrile (200 ml) was refluxed for 3 hours. The reaction was poured into H2O and 7.1 g of a beige solid was collected. The filtrate was extracted with dichloromethane, and after concentration an additional 6.7 g of crude solid was harvested. The solids were combined and triturated with refluxing ethyl acetate to afford 8.0 g of 6-fluoro-3-[1-(3-hydroxypropyl)-4-piperidinyl]-1,2-benzisoxazole as an off-white solid. A sample (4.0 g) was recrystallized from ethanol-water (with charcoal treatment) to yield 2.4 g (40%) of the alcohol as a white solid, m.p.=140°-142° C.

Aufarbeitung

  1. temperaturewas refluxed for 3 hours
  2. customwas collected
  3. extractionThe filtrate was extracted with dichloromethane
  4. concentrationafter concentration an additional 6.7 g of crude solid
  5. customtriturated with refluxing ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a0f91a1e633d4a06b0b44c7bbdda05ed
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597842

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