Water → 4-(4-Acetoxy-4-(4-chlorophenyl)-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone

HRID 1722308

Reaktionsgleichung

Reaktionsgleichung von HRID 1722308
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:26])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[O:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].O>N1C=CC=CC=1>[C:27]([O:26][C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][C:17]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)=[O:18])[CH2:12][CH2:13]1)(=[O:29])[CH3:28]

Komponenten

5

Edukt 3

HCID 962WaterHCID 3559HaloperidolHCID 7918Acetic Anhydride

Produkt 1

HCID 233649954-(4-Acetoxy-4-(4-chlorophenyl)-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

4-(4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone (20 g) and acetic acid anhydride (16 g) in 200 ml of dried pyridine (KOH pellets) were refluxed for 2 h. The mixture was poured into cold H2O (0° C.) (2 liters) and extracted with isopropylether (2×200 ml). The combined organic phases were dried (MgSO4) and the solvent evaporated. The title compound was obtained after column chromatography on silica gel (eluent, ethyl acetate/dichloromethane/methanol, 1:1:1). Yield 10.6 g (48%). Mp 106°-110° C. (from isopropyl ether). The hydrochloride salt was precipitated from acetone. Mp 215° C. According to TLC analysis the content of Haloperidol was 0.5%.

Aufarbeitung

  1. extractionextracted with isopropylether (2×200 ml)
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-53776443e02a432395057d3a40d75a82
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04855307

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