Water → Benzyl 3-oxopiperazine-1-carboxylate

HRID 457482Notes

Reaction equation

HRID 457482 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8ca9dbdf99024d6ca2c202c453609960
Source dataset
uspto-grants-2007_03
Patent number
US07189715B2

Reaction notes

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