Sodium Bicarbonate → HCID 14837053, Verbindung

HRID 2072808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2072808
C(=O)(O)[O-].[Na+].[F:6][C:7]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:8]=1[O:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Cl[CH2:25][CH2:26][CH2:27][C:28]1[C:32]2[CH:33]=[C:34]([O:39][CH3:40])[C:35]([O:37][CH3:38])=[CH:36][C:31]=2[O:30][N:29]=1>CN(C)C=O.[I-].[K+]>[CH3:40][O:39][C:34]1[C:35]([O:37][CH3:38])=[CH:36][C:31]2[O:30][N:29]=[C:28]([CH2:27][CH2:26][CH2:25][N:13]3[CH2:14][CH2:15][CH:10]([O:9][C:8]4[C:16]([F:23])=[C:17]([F:22])[C:18]([F:21])=[C:19]([F:20])[C:7]=4[F:6])[CH2:11][CH2:12]3)[C:32]=2[CH:33]=1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 148370404-(2,3,4,5,6-Pentafluorophenoxy)piperidineHCID 14837050HCID 14837050, Verbindung

Produkt 1

HCID 14837053HCID 14837053, VerbindungAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 10 g of sodium bicarbonate, 0.12 g of potassium iodide, 5.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine and 75 ml of dimethylformamide was treated with a solution of 5.37 g of 3-(3-chloropropyl)-5,6-dimethoxy-1,2-benzisoxazole in 25 ml dimethylformamide and stirred for five hours at 70° C. The reaction mixture was filtered and the filtrate poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering, evaporation under reduced pressure afforded a residue which was purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate) to yield 5.5 g of 1-[(5,6-dimethoxy-1,2-benzisoxazol-3-yl)propyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine as a waxy solid. This material was dissolved in isopropanol and acidified to pH 1 with etheral hydrogen chloride to precipitate the corresponding hydrochloride salt. Recrystallization from isopropanol afforded 3.3 g (36%) of 1-[(5,6-dimethoxy- 1,2-benzisoxazol-3-yl)propyl]-4-(2,3,4,5, 6-pentafluorophenoxy)piperidine hydrochloride, m.p. 210°-212° C.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate poured into water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering
  7. customevaporation under reduced pressure
  8. customafforded a residue which
  9. customwas purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-75f2d8b75943487eacc71c0073258941
Quelldatensatz
uspto-grants-1990_04
Patentnummer
US04914204

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