tert-Butyl piperazine-1-carboxylate → t-Butyl 4-(6-chloromethylpyridin-2-ylmethyl)piperazine-1-carboxylate

HRID 1172240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172240
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][Cl:10])[N:4]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>C(O)C>[Cl:10][CH2:9][C:5]1[N:4]=[C:3]([CH2:2][N:21]2[CH2:20][CH2:19][N:18]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH2:23][CH2:22]2)[CH:8]=[CH:7][CH:6]=1

Komponenten

4

Edukt 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 3166542,6-Bis(chloromethyl)pyridine

Produkt 1

HCID 58105228t-Butyl 4-(6-chloromethylpyridin-2-ylmethyl)piperazine-1-carboxylateAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2,6-Bis(chloromethyl)pyridine (352 mg) was suspended in 4 mL of ethanol, and 372 mg of N-(t-butoxycarbonyl)piperazine was added into the suspension at ice temperature, and then the suspension was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the residue was added to water and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by chromatography on silica gel (methylene chloride-ethanol=30:1) to give 250 mg of t-butyl 4-(6-chloromethylpyridin-2-ylmethyl)piperazine-1-carboxylate as a colorless oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was added to water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified by chromatography on silica gel (methylene chloride-ethanol=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-121de2dfe1c348688735dfe174298699
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834002B2

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