Water → Benzyl 3-oxopiperazine-1-carboxylate

HRID 272412

Reaktionsgleichung

Reaktionsgleichung von HRID 272412
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].C([O-])([O-])=O.[K+].[K+].O.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C1COCC1>[CH2:19]([O:18][C:16]([N:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 231360Piperazin-2-one

Produkt 1

HCID 736777Benzyl 3-oxopiperazine-1-carboxylateAusbeute 146 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a magnetically stirred solution of piperazin-2-one (2.0 g, 20.0 mmol) in THF (10 mL) at room temperature under Ar atmosphere, K2CO3 (8.25 g, 120 mmol), water (10 mL), and benzyl chloroformate (3.14 mL, 22.0 mmol) were added. The reaction mixture was stirred for 18 hours at room temperature. Water (50 mL) was added, and the aqueous phase was extracted with EtOAc (2×100 mL). The combined organic layers were washed with water, dried with MgSO4, and concentrated in vacuo to the give the title compound (6.84 g, 100%). 1H NMR (400 MHz, CDCl3) δ 3.37 (bs, 2H), 3.68 (t, J=4.7 Hz, 2H), 4.13 (s, 2H), 5.14 (s, 2H), 7.34 (m, 5H).

Aufarbeitung

  1. extractionthe aqueous phase was extracted with EtOAc (2×100 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo to the

Quellen und Nachweise

ORD-Eintrag
ord-3d728791d8b94af4abfdea798f2face4
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456173B2

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