Potassium Carbonate → tert-Butyl 4-(3-fluoro-2-nitrophenyl)piperazine-1-carboxylate

HRID 730553Notes

Reaction equation

HRID 730553 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23](F)[C:22]=1[N+:28]([O-:30])=[O:29]>CS(C)=O.C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([F:20])[C:22]=2[N+:28]([O-:30])=[O:29])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 879221,3-Difluoro-2-nitrobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 53255497tert-Butyl 4-(3-fluoro-2-nitrophenyl)piperazine-1-carboxylateYield 96.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of piperazine-1-carboxylic acid tert-butyl ester (0.204 g, 1.1 mmol) in 1 mL dimethylsulfoxide was added potassium carbonate (0.303 g, 2.2 mmol) followed by 1,3-difluoro-2-nitro-benzene (0.159 g, 1 mmol). The solution was stirred 30 minutes at room temperature, and was then diluted with 50 mL ethyl ether. The organic phase was washed three times with 50 mL water and once with 50 mL brine, dried over sodium sulfated, and concentrated in vacuo to give 0.314 g (0.965 mmol, 96.5%) of 4-(3-fluoro-2-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester as a yellow oil. MS: 226 (M−BOC+H)+.

Workup

  1. washThe organic phase was washed three times with 50 mL water
  2. dry with materialonce with 50 mL brine, dried over sodium
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d3fca98337941339da1d482c71bd679
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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