Di-tert-butyl dicarbonate → Tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylate

HRID 885855Notes

Reaction equation

HRID 885855 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[O:16](C(OC(C)(C)C)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O>C(Cl)Cl>[C:20]([O:19][C:17]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10]([C:13](=[O:15])[CH3:14])=[CH:11][CH:12]=2)[CH2:2][CH2:3]1)=[O:16])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 97269Piperazin-4-ylacetophenone

Product 1

HCID 21136190Tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylateYield 91.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-piperazin-1-yl-phenyl)-ethanone (513 mg, 2.51 mmol), BOC2O (820 mg, 3.76 mmol) and TEA (0.698 ml, 5.02 mmol) in DCM (20 ml) was stirred at room temperature overnight. The resulting solution was concentrated in vacuo and then partitioned between water and AcOEt. The organic phase was dried over Na2SO4, evaporated in vacuo and the crude reaction mixture was purified by column chromatography (eluent: petroleum ether/AcOEt) to give 701 mg of 4-(4-acetyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. custompartitioned between water and AcOEt
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated in vacuo
  5. customthe crude reaction mixture
  6. customwas purified by column chromatography (eluent: petroleum ether/AcOEt)

Sources & evidence

ORD record
ord-322c425e730140db890cb8ed1bd5e8c2
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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