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

HRID 2085424

Reaktionsgleichung

Reaktionsgleichung von HRID 2085424
[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

A solution of 4-Acetyl-4-phenylpiperidine (7, 1.53 g, 7.50 mmol), 3-bromo-propylamine hydrobromide (1.64 g, 7.50 mmol) and potassium carbonate (1.24 g, 9.00 mmol) was stirred in refluxing 1,4-dioxane (50 mL) for 12 h. 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 magnesium sulfate and concentrated. The residue was purified by flash chromatography (EtOAc-MeOH-Et3N 100/40/20), giving the desired product as a colorless oil (780 mg, 40%): 1H NMR δ 1.56 (p, J=7 Hz, 2 H), 1.84 (s, 3 H), 1.98 (m, 2 H), 2.15 (br t, J=12 Hz, 2 H), 2.29 (t, J=7 Hz, 2 H), 2.41 (br d, J=12 Hz, 2 H), 2.66 (t, J=7 Hz, 4 H), 7.18-7.30 (m, 5 H); 13C NMR δ 26.28, 31.11, 33.43, 41.47, 51.62, 55.31, 57.19, 77.32, 77.74, 78.17, 126.95, 127.69, 129.44, 142.25, 210.15.

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 magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (EtOAc-MeOH-Et3N 100/40/20)

Quellen und Nachweise

ORD-Eintrag
ord-ade208900c2d442b9d4e9cf3ed4d739f
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720324B2

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