Sodium Bicarbonate → tert-Butyl 3-(4-benzylpiperazin-1-yl)piperidine-1-carboxylate

HRID 1643960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643960
Cl.[CH2:2]([N:9]([CH2:13][CH2:14]Cl)[CH2:10][CH2:11]Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[NH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]1.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:2]([N:9]1[CH2:13][CH2:14][N:17]([CH:18]2[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochlorideHCID 177503343-Aminopiperidine hydrochloride, N1-BOC protected

Produkt 1

HCID 86642500tert-Butyl 3-(4-benzylpiperazin-1-yl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4.90 g (21.1 mmol) of benzylbis(2-chloroethyl)amine hydrochloride were dissolved in ethanol (120 ml) and, while stirring, 5.00 g (21.1 mmol) of tert-butyl 3-aminopiperidine-1-carboxylate hydrochloride and 14.2 g (169 mmol) of sodium bicarbonate were added. The resulting reaction solution was heated under reflux for 4 h. The cooled reaction mixture was concentrated in vacuo, 100 ml of water were added, and the aqueous phase was extracted with ethyl acetate (4×60 ml). The combined organic phases were washed with saturated aqueous NaHCO3 solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (mobile phase gradient 0-5% methanol in dichloromethane). Yield: 6.99 g (75%) of yellow solid

Aufarbeitung

  1. customThe resulting reaction solution
  2. temperaturewas heated
  3. temperatureunder reflux for 4 h
  4. customThe cooled reaction mixture
  5. concentrationwas concentrated in vacuo, 100 ml of water
  6. additionwere added
  7. extractionthe aqueous phase was extracted with ethyl acetate (4×60 ml)
  8. washThe combined organic phases were washed with saturated aqueous NaHCO3 solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by chromatography on silica gel (mobile phase gradient 0-5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-da4c5a17c36e4fcc914bbcd43242ca4a
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119676B2

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