Water → 1-[3-[4-[(4-Fluorophenyl)(4-methylthien-2-yl)methylene]piperidin-1-ylmethyl]benzoyl]piperidine

HRID 840165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 840165
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:31]2[S:32][CH:33]=[C:34]([CH3:36])[CH:35]=2)=[C:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:20][CH:19]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:31]2[S:32][CH:33]=[C:34]([CH3:36])[CH:35]=2)=[C:25]2[CH2:30][CH2:29][N:28]([CH2:2][C:3]3[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=3)[C:6]([N:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:7])[CH2:27][CH2:26]2)=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 100144051-[3-(Chloromethyl)benzoyl]piperidineHCID 110770424-[(4-Fluorophenyl)(4-methylthien-2-yl)methylene]piperidine

Produkt 1

HCID 99571511-[3-[4-[(4-Fluorophenyl)(4-methylthien-2-yl)methylene]piperidin-1-ylmethyl]benzoyl]piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of this benzoyl piperidine (2.3 9), the above 4-[(4-fluorophenyl)(4-methylthien-2-yl)methylene]piperidine (3 g) and triethylamine (3 ml) in toluene was boiled under reflux for 5 h. Water was added to the cooled mixture, the layers were separated and the toluene layer was separated, washed with brine, dried over sodium sulphate and evaporated. The resultant oil (5.6 g) was dissolved in dichloromethane and chromatographed on silica. Elution with dichloromethane/ammonium hydroxide (1%) containing increasing amounts of methanol gave fractions that on evaporation gave the title compound (4.36 g). A solution of this compound in ether was treated with with an ethereal solution of hydrogen chloride. The precipitate was collected and dried to give the hydrochloride salt (3.6 g) m.p. 118-142° C.

Aufarbeitung

  1. temperatureunder reflux for 5 h
  2. customthe layers were separated
  3. customthe toluene layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. dissolutionThe resultant oil (5.6 g) was dissolved in dichloromethane
  8. customchromatographed on silica
  9. washElution with dichloromethane/ammonium hydroxide (1%)
  10. additioncontaining
  11. temperatureincreasing amounts of methanol
  12. customgave fractions that
  13. customon evaporation

Quellen und Nachweise

ORD-Eintrag
ord-527ef3e360ce434289e48d02115ab13a
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06365604B1

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