Isopropanol → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(1-hydroxyethyl)-4-phenylpiperidine hydrochloride

HRID 745333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 745333
CC(O)C.[ClH:5].[C:6]([C:9]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]2[C:22]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=3[O:20][N:19]=2)[CH2:11][CH2:10]1)(=[O:8])[CH3:7].[BH4-].[Na+]>CO>[ClH:5].[F:27][C:25]1[CH:24]=[CH:23][C:22]2[C:18]([CH2:17][CH2:16][CH2:15][N:12]3[CH2:11][CH2:10][C:9]([CH:6]([OH:8])[CH3:7])([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:14][CH2:13]3)=[N:19][O:20][C:21]=2[CH:26]=1

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 133198744-Acetyl-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-phenylpiperidine hydrochloride

Produkt 1

HCID 133198761-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(1-hydroxyethyl)-4-phenylpiperidine hydrochlorideAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 50 ml of 2-propanol and 10 ml of methanol, was added 2.8 g of 4-acetyl-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-phenylpiperidine hydrochloride and 0.76 g of sodium borohydride. After stirring at ambient temperature for twenty hrs, the mixture was evaporated. The residue was stirred with 100 ml of water for ten mins and then extracted with ether. The ether extract was washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the ether solution was acidified to pH 1 with ethereal hydrogen chloride. The resultant precipitate was collected and dried to give 2.3 g (78%) of product, mp 80° C. Recrystallization from ethyl acetate/methanol (9:1) gave the analytical sample, mp 143°-147° C.

Aufarbeitung

  1. customthe mixture was evaporated
  2. stirringThe residue was stirred with 100 ml of water for ten mins
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with water (2×), saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtering
  8. customThe resultant precipitate was collected
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-62d6a3a538994177a65b174384f1defe
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04598152

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