Benzyl Bromide → Tert-butyl 4-benzyl-3-oxopiperazine-1-carboxylate

HRID 38299

Reaction equation

HRID 38299 reaction equation
[H-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][NH:13][C:12](=[O:16])[CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[O:16]=[C:12]1[N:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:15][N:10]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:11]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 10891590Tert-butyl 4-benzyl-3-oxopiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (88 mg, 60% wt.) was added portionwise to a solution of 4-BOC-piperazinone (400 mg) in DMF (10 ml). The reaction mixture was stirred for 1 h, and then benzyl bromide (262 μl) was added dropwise and the mixture stirred at room temp for 16 h. The reaction was quenched with methanol and diluted with water, and then extracted with EtOAC. The organic extracts were concentrated in vacuo and the residue was purified by chromatography (silica, 20% ether/hexane as eluent) to give the sub-title compound (429 mg).

Workup

  1. stirringthe mixture stirred at room temp for 16 h
  2. customThe reaction was quenched with methanol
  3. additiondiluted with water
  4. extractionextracted with EtOAC
  5. concentrationThe organic extracts were concentrated in vacuo
  6. customthe residue was purified by chromatography (silica, 20% ether/hexane as eluent)

Sources & evidence

ORD record
ord-986826fa224b44c498e4e63b28714e72
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Linked notes

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