Potassium Iodide → 3-(4-Cyano-4-phenylpiperidin-1-yl)propylphthalimide

HRID 278918

Reaktionsgleichung

Reaktionsgleichung von HRID 278918
Cl.[C:2]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)#[N:3].Br[CH2:17][CH2:18][CH2:19][C:20]1[CH:30]=[CH:29][CH:28]=[C:22]2[C:23]([NH:25][C:26](=[O:27])[C:21]=12)=[O:24].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[C:2]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:6][N:7]([CH2:17][CH2:18][CH2:19][C:20]2[CH:30]=[CH:29][CH:28]=[C:22]3[C:23]([NH:25][C:26](=[O:27])[C:21]=23)=[O:24])[CH2:8][CH2:9]1)#[N:3]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 30849734-Phenylpiperidine-4-carbonitrile hydrochlorideHCID 21958088Bromopropylphthalimide

Produkt 1

HCID 227252233-(4-Cyano-4-phenylpiperidin-1-yl)propylphthalimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 4-cyano-4-phenylpiperidine hydrochloride (111 g, 0.5 mol), 3-bromopropylphthalimide (135.39 g, 0.505 mol), potassium carbonate (276.42 g, 2 mol), and potassium iodide (5.4 g) in DMF (1 L) was stirred and heated at 100-110° C. for 8 hours. About 80% of the solvent was evaporated at reduced pressure, the residue was diluted with dichloromethane (1 L) and washed with brine (3×300 mL) and dried (Na2SO4). Solvent was evaporated from the dichloromethane solution and the residue was treated with isopropanol (400 mL) and cooled. The pale yellow crystalline product formed was filtered, washed with ice-cold isopropanol and dried (168.6 g, 90%); M.p. 96-98° C.

Aufarbeitung

  1. customAbout 80% of the solvent was evaporated at reduced pressure
  2. additionthe residue was diluted with dichloromethane (1 L)
  3. washwashed with brine (3×300 mL)
  4. dry with materialdried (Na2SO4)
  5. customSolvent was evaporated from the dichloromethane solution
  6. additionthe residue was treated with isopropanol (400 mL)
  7. temperaturecooled
  8. customThe pale yellow crystalline product formed
  9. filtrationwas filtered
  10. washwashed with ice-cold isopropanol
  11. customdried (168.6 g, 90%)

Quellen und Nachweise

ORD-Eintrag
ord-580537028e0e433ca7b4df9366a19cd3
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362182B1

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