Potassium Carbonate → 1-(3-Aminopropyl)-4-methoxycarbonyl-4-phenylpiperidine

HRID 278913

Reaktionsgleichung

Reaktionsgleichung von HRID 278913
[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].Br.Br[CH2:19][CH2:20][CH2:21][NH2:22].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:7][N:8]([CH2:19][CH2:20][CH2:21][NH2:22])[CH2:9][CH2:10]1)=[O:4]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 787013-Bromopropylamine hydrobromideHCID 545827Methyl 4-phenylpiperidine-4-carboxylate

Produkt 1

HCID 106838831-(3-Aminopropyl)-4-methoxycarbonyl-4-phenylpiperidineAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 4-methoxycarbonyl-4-phenylpiperidine (8.5 g, 0.039 mol), 3-bromopropylamine hydrobromide (12.7 g, 0.058 mol), potassium carbonate (13.475 g, 0.0957 mole), and KI (3.24 g, 0.0195 mol) in 1,4-dioxane (200 mL) was stirred and refluxed for 24 hours. Dioxane was evaporated at reduced pressure, the residue was treated with ice-cold 6 N NaOH (400 mL) and extracted with CH2Cl2 (4×120 mL). Solvent was evaporated from the combined dried (K2CO3) extracts and the residue was purified by column chromatography on silica gel using CHCl3/MeOH/ 2 M NH3 in MeOH (20:2:1) as the eluent to afford the product as a viscous oil (7.8 g, 72%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-677c6f41a62f435fb570a025c45b1ad5
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362182B1

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