Benzyl Bromide → Ethyl 1-benzylpiperidine-3-carboxylate

HRID 432816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432816
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH2:12]([N:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

4

Edukt 2

HCID 7498Benzyl BromideHCID 98969Ethyl nipecotate

Produkt 1

HCID 2736370Ethyl 1-benzylpiperidine-3-carboxylateAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Commercially available ethyl nipecotate (509.7 mg; 3.25 mmol) was dissolved in dichloromethane (12 ml). Dilsopropylethylamine (570 μl; 3.27 mmol) was added, followed by commercially available benzyl bromide (386 μl; 3.25 mmol) and the mixture stirred at ambient temperature for approximately 20 hours. The mixture was then evaporated at ambient temperature under reduced pressure. The crude product was purified by chromatography on silica eluting with 80% ethyl acetate in hexane, giving ethyl 1-benzyl-3-piperidinecarboxylate (634.4 mg) as a colorless oil. MS m/z (positive ion) 248 (MH+; 100).

Aufarbeitung

  1. additionDilsopropylethylamine (570 μl; 3.27 mmol) was added
  2. customThe mixture was then evaporated at ambient temperature under reduced pressure
  3. customThe crude product was purified by chromatography on silica eluting with 80% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-83ed16de13cb428d92e81f5610e6e879
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664271B1

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