tert-Butyl piperazine-1-carboxylate → 2-(3-Nitrophenyl)-1-(piperazin-1-yl)ethanone

HRID 1892144Notes

Reaction equation

HRID 1892144 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11](Cl)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[N:14]1(C(OC(C)(C)C)=O)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5232253-Nitrobenzeneacetyl chloride

Product 1

HCID 687285592-(3-Nitrophenyl)-1-(piperazin-1-yl)ethanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-(3-nitrophenyl)acetyl chloride (0.20 ml, 1.0 mmol.) was added to a vigorously stirred mixture of tert-butyl piperazine-1-carboxylate (0.19 g, 1.0 mmol.) in CH2Cl2 (2 ml) and sat. aq. NaHCO3 (1 ml). The reaction was stirred for 1 hour; then the organic layer was separated, filtered through a plug of MgSO4, and concentrated under vacuum. The residue was treated with TFA in CH2Cl2 to remove the Boc group to give 2-(3-nitrophenyl)-1-(piperazin-1-yl)ethanone, which was carried on crude.

Workup

  1. customthen the organic layer was separated
  2. filtrationfiltered through a plug of MgSO4
  3. concentrationconcentrated under vacuum
  4. additionThe residue was treated with TFA in CH2Cl2
  5. customto remove the Boc group

Sources & evidence

ORD record
ord-aeb5bc8838be4882a5e973d7c9da4429
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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