Hydrochloric Acid → 1-{2-{N-[4-(4-Fluorophenyl)-4-oxobutyl]-N-methylamino}ethyl}-4-(4-chlorophenoxy)piperidine dihydrochloride

HRID 463323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 463323
[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]([Cl:35])=[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+].[Na+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>CO>[ClH:35].[ClH:1].[F:3][C:4]1[CH:5]=[CH:6][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:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[CH2:26][CH2:27]2)[CH3:19])=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 20283107HCID 20283107, Verbindung

Produkt 1

HCID 202830801-{2-{N-[4-(4-Fluorophenyl)-4-oxobutyl]-N-methylamino}ethyl}-4-(4-chlorophenoxy)piperidine dihydrochlorideAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 8.94 g (17.7 mmol) of 1-{2-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}ethyl}-4-(4-chlorophenoxy)piperidine dihydrochloride, 135 ml of methanol, and 55 ml of 3N HCl was heated at reflux for 3 hours under nitrogen. The mixture was allowed to cool to room temperature, poured into saturated sodium carbonate, extracted twice with ether and dried over potassium carbonate. Filtration followed by evaporation of the solvent provided an oil. The yield of a crude dihydrochloride was 6.71 g (81%). Recrystallization from ethanol provided 2.37 g (28%) of the desired ketone.

Aufarbeitung

  1. temperatureat reflux for 3 hours under nitrogen
  2. extractionextracted twice with ether
  3. dry with materialdried over potassium carbonate
  4. filtrationFiltration
  5. customfollowed by evaporation of the solvent
  6. customprovided an oil
  7. customRecrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4e55e6e76f4440a19cf54d9609105e0e
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04518713

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