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Hydrochloric Acid → 1-{2-{N-[4-(4-fluorophenyl)-4-oxobutyl]-N-methylamino}ethyl}-4-(4-trifluoromethyl-phenoxy)piperidine dihydrochloride

HRID 463316
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 463316
[ClH:1].Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:15][CH2:16][CH2:17][N:18]([CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([O:28][C:29]4[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=4)[CH2:24][CH2:23]3)[CH3:19])OCC[O:11]2)=[CH:6][CH:5]=1.Cl.C(=O)(O)[O-].[Na+]>CO>[ClH:1].[ClH:1].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:11])[CH2:15][CH2:16][CH2:17][N:18]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH:25]([O:28][C:29]3[CH:30]=[CH:31][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:34]=3)[CH2:26][CH2:27]2)[CH3:19])=[CH:6][CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20283118HCID 20283118, Verbindung

Produkt 1

HCID 202830661-{2-{N-[4-(4-fluorophenyl)-4-oxobutyl]-N-methylamino}ethyl}-4-(4-trifluoromethyl-phenoxy)piperidine dihydrochlorideAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

A solution of 3.75 g (6.38 mmol) of 1-{2-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}ethyl}-4-(4-trifluoromethylphenoxy)piperidine dihydrochloride, 55 ml of methanol, and 22.5 ml of 3N HCl was heated at reflux under nitrogen for 3 hours. The reaction mixture was allowed to cool to room temperature and was subsequently neutralized with sodium bicarbonate. The methanol was evaporated and the residue made basic with sodium carbonate. The mixture was extracted with ether, washed with saturated sodium chloride and dried over potassium carbonate. Filtration followed by evaporation of the solvent provided an oil. The dihydrochloride was recrystallized from acetonitrile to provide 1.75 g (50%) of 1-{2-{N-[4-(4-fluorophenyl)-4-oxobutyl]-N-methylamino}ethyl}-4-(4-trifluoromethyl-phenoxy)piperidine dihydrochloride.

Aufarbeitung

  1. temperatureat reflux under nitrogen for 3 hours
  2. customThe methanol was evaporated
  3. extractionThe mixture was extracted with ether
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over potassium carbonate
  6. filtrationFiltration
  7. customfollowed by evaporation of the solvent
  8. customprovided an oil
  9. customThe dihydrochloride was recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-1d447255fea3442db5613277fe232cfa
Quelldatensatz
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04518713

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