Potassium Carbonate → 4-Acetyl-1-(3-aminopropyl)-4-phenylpiperidine

HRID 382704

Reaktionsgleichung

Reaktionsgleichung von HRID 382704
[C:1]([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)(=[O:3])[CH3:2].Br.Br[CH2:18][CH2:19][CH2:20][NH2:21].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:1]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:6][N:7]([CH2:18][CH2:19][CH2:20][NH2:21])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 787013-Bromopropylamine hydrobromideHCID 1015214-Acetyl-4-phenylpiperidine

Produkt 1

HCID 105874474-Acetyl-1-(3-aminopropyl)-4-phenylpiperidineAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4-Acetyl-4-phenylpiperidine (1.53 g, 7.50 mmol, 1.00 equiv, Aldrich), 3-bromopropylamine hydrobromide (1.64 g, 7.50 mmol, 1.00 equiv) and potassium carbonate (1.24 g, 9.00 mmol, 1.20 equiv) were stirred in refluxing 1,4-dioxane (50 mL) for 12 hours. After removal of dioxane, water (50 mL) was added and the pH was adjusted to 11-12 by addition of 1 N aqueous NaOH. The mixture was extracted with CH2Cl2 (100 mL+3×50 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (EtOAc-MeOH-Et3N 100:40:20) to give 780 mg (40%) of colorless oil, which was characterized spectroscopically.

Aufarbeitung

  1. customAfter removal of dioxane, water (50 mL)
  2. additionwas added
  3. additionthe pH was adjusted to 11-12 by addition of 1 N aqueous NaOH
  4. extractionThe mixture was extracted with CH2Cl2 (100 mL+3×50 mL)
  5. dry with materialThe combined organic solutions were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (EtOAc-MeOH-Et3N 100:40:20)

Quellen und Nachweise

ORD-Eintrag
ord-56096f2314a24c39b639dc00cc41220e
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310076B1

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