Potassium Carbonate → 3-(4-Ethoxycarbonyl-4-phenylpiperidin-1-yl)propylamine

HRID 382764

Reaktionsgleichung

Reaktionsgleichung von HRID 382764
[CH2:1]([O:3][C:4]([C:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].Br.Br[CH2:20][CH2:21][CH2:22][NH2:23].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:8][N:9]([CH2:20][CH2:21][CH2:22][NH2:23])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 32414NormeperidineHCID 787013-Bromopropylamine hydrobromide

Produkt 1

HCID 105895973-(4-Ethoxycarbonyl-4-phenylpiperidin-1-yl)propylamineAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 4-ethoxycarbonyl-4-phenylpiperidine (30.5 g, 0.131 mol), 3-bromopropylamine hydrobromide (42.93 g, 0.196 mol), potassium carbonate (36.14 g, 0.241 mole), and KI (10.8 g, 0.065 mol) in 1,4-dioxane (500 mL) was stirred and refluxed for 24 hours. Dioxane was evaporated at reduced pressure, the residue was treated with ice-cold 6N NaOH (400 mL) and extracted with CH2Cl2 (4×120 mL). Solvent was evaporated from the combined dried (K2CO3) CH2Cl2 extracts and the residue was purified by column chromatography on silica gel using CHCl3/MeOH/2M NH3 in MeOH (20:2:1) as the eluent to afford the product as a viscous oil (24.2 g, 83.3%).

Aufarbeitung

  1. temperaturerefluxed for 24 hours
  2. customDioxane was evaporated at reduced pressure
  3. additionthe residue was treated with ice-cold 6N NaOH (400 mL)
  4. extractionextracted with CH2Cl2 (4×120 mL)
  5. customSolvent was evaporated from the
  6. dry with materialcombined dried (K2CO3) CH2Cl2 extracts
  7. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a47d4c7073c1402cb84794f3d01b68c9
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310076B1

Verknüpfte Notizen

Wird geladen…