Sodium Iodide → Methyl 4-(3,4-dichlorophenoxy)-1-piperidinebutanoate

HRID 915539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915539
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:8][CH2:7]1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 37320424-(3,4-Dichlorophenoxy)piperidine

Produkt 1

HCID 69417722Methyl 4-(3,4-dichlorophenoxy)-1-piperidinebutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

4-(3,4-Dichlorophenoxy)piperidine (4.15 g) was dissolved in acetone (80 ml). Potassium carbonate (2.42 g), sodium iodide (0.49 g) and then methyl 4-bromobutyrate (1.95 ml) were added and the mixture was stirred for 42 h. The solvent, was evaporated and the residue was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The organic phases were dried (MgSO4), filtered and evaporated and the residue was chromatographed eluting with ethyl acetate: triethylamine (99:1) to give the subtitle compound (4.52 g).

Aufarbeitung

  1. customThe solvent, was evaporated
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was chromatographed
  8. washeluting with ethyl acetate: triethylamine (99:1)

Quellen und Nachweise

ORD-Eintrag
ord-6e42b245ec7a42478dab5d862e88db9b
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265227B2

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