Benzyl chloroformate → Benzyl 2-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 377198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377198
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][OH:9].[OH-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>O1CCOCC1>[CH2:16]([O:15][C:13]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][OH:9])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 151442-Piperidin-2-ylethanol

Produkt 1

HCID 45358666Benzyl 2-(2-hydroxyethyl)piperidine-1-carboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Piperidine ethanol (39.6 ml, 0.31 mol) was dissolved in 5M aq NaOH (62 ml, 0.31 mol) and dioxan (100 ml). The mixture was cooled to 0° C. and treated with benzyl chloroformate (45.3 ml, 0.32 mol) and 5M NaOH (62 ml, 0.31 mol). Stirring was continued at room temp. for 18 hours. Dioxan was removed in vacuo and the aqueous phase extracted with ether before acidifying with 5N HCl and extracting again with ether. The organic phase was dried and evaporated in vacuo and the residue purified by chromatography on silica gel to give the title compound (77.2 g. 95%). MH+ 264.

Aufarbeitung

  1. customDioxan was removed in vacuo
  2. extractionthe aqueous phase extracted with ether
  3. extractionextracting again with ether
  4. customThe organic phase was dried
  5. customevaporated in vacuo
  6. customthe residue purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a73adbc824284e41a9fbe67c1543a175
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025367

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