Potassium Carbonate → 4-(3-Chlorophenoxy)piperidine

HRID 463306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 463306
CNCCCC1(C2C=CC(F)=CC=2)OCCO1.C(=O)([O-])[O-].[K+].[K+].BrCC([N:28]1[CH2:33][CH2:32][CH:31]([O:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=2)[CH2:30][CH2:29]1)=O.C(=O)(O)[O-].[Na+].C(O)(=O)C(O)=O.FC1C=CC(C2(CCCN(CC(N3CCC(OC4C=CC=C(Cl)C=4)CC3)=O)C)OCCO2)=CC=1>C(O)C>[Cl:41][C:37]1[CH:36]=[C:35]([CH:40]=[CH:39][CH:38]=1)[O:34][CH:31]1[CH2:30][CH2:29][NH:28][CH2:33][CH2:32]1

Komponenten

7

Edukt 5

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 133357082-[3-(Methylamino)propyl]-2-(4-fluorophenyl)-1,3-dioxolaneHCID 20283061N-(2-bromoacetyl)-4-(m-chlorophenoxy)piperidineHCID 202831291-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(3-chlorophenoxy)piperidine oxalate

Produkt 1

HCID 27353174-(3-Chlorophenoxy)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a suspension of 2-[3-(methylamino)propyl]-2-(4-fluorophenyl)-1,3-dioxolane (7.2 g, 30.0 mmol), potassium carbonate (10.6 g, 76.8 mmol) and 120 ml of ethanol at 0° was added dropwise a solution of N-(2-bromoacetyl)-4-(3-chlorophenoxy)piperidine (11.3 g, 34.0 mmol) in 120 ml of ethanol. The solution was stirred 1 hour at room temperature and at reflux for 1 hour. The mixture was poured into saturated sodium bicarbonate, extracted with methylene chloride, washed with water and dried over magnesium sulfate. Filtration followed by evaporation of the solvent provided an oil. Yield: 11.0 g of 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(3-chlorophenoxy)piperidine oxalate. Yield from 4-(3-chlorophenoxy)piperidine: 43%; from N-(2-bromoacetyl)-4-(3-chlorophenoxy)piperidine: 77%.

Aufarbeitung

  1. temperatureat reflux for 1 hour
  2. extractionextracted with methylene chloride
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation of the solvent
  7. customprovided an oil

Quellen und Nachweise

ORD-Eintrag
ord-36976273ec844bba84cba99274933333
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04518713

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