Acetone → Ethyl 1-(2-chloroethyl)piperidine-4-carboxylate

HRID 1724886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724886
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3](C(OCC)=O)[CH2:2]1.Br[CH2:13][CH2:14][Cl:15].[C:16]([O-:19])([O-])=[O:17].[K+].[K+].[CH3:22][C:23](C)=O>>[Cl:15][CH2:14][CH2:13][N:1]1[CH2:2][CH2:3][CH:9]([C:16]([O:19][CH2:22][CH3:23])=[O:17])[CH2:10][CH2:11]1

Komponenten

5

Edukt 4

HCID 180AcetoneHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 98969Ethyl nipecotate

Produkt 1

HCID 61287119Ethyl 1-(2-chloroethyl)piperidine-4-carboxylateAusbeute 38,6 %

Versuchsvorschrift

To a solution of ethyl nipecotate (20.0 mL, 130 mmol) in acetone (180 mL) was added 1-bromo-2-chloroethane (21.6 mL, 260 mmol) followed by anhydrous K2CO3 (27.12 g, 196 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (75 mL) and extracted with Et2O. The combined organic layers were dried with MgSO4, filtered, and concentrated under vacuum. Purification of the crude residue by flash chromatography (50% Et2O/50% hexane) on silica gel gave the title compound (10.99 g, 38.6%). EI-MS m/z 220(M+H+) Rt (1.20 min).

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. additionThe resulting residue was treated with H2O (75 mL)
  3. extractionextracted with Et2O
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification of the crude residue by flash chromatography (50% Et2O/50% hexane) on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c6de050ff7d8409a86d65613d38ab3cf
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07488827B2

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