Potassium Carbonate → Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate

HRID 2236529Notes

Reaction equation

HRID 2236529 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[I+].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:14]2[CH2:13][CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 8176205-Bromo-2-nitropyridineHCID 178449043HCID 178449043, compound

Product 1

HCID 11243758Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylateYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3 g (14.78 mmol) of 5-bromo-2-nitropyridine, 5.5 g (29.56 mmol) of tert-butyl 1-piperazinecarboxylate, 5.46 g (14.78 mmol) of tetra-butylammonium iodine and 4.1 g (29.56 mmol) of potassium carbonate were placed in a flask. Dimethylsulfoxide (45 mL) is added and heat up to 80° C. for 24 hours. After cooling to room temperature, the precipitate is filtered and washed with ethyl acetate. Excess amount of water is added and extracted 4×. Dried with sodium sulfate and evaporated to give 2.7 g (59% yield) as a yellow solid. MS (ESI) m/z 309.1(M+1)

Workup

  1. customwere placed in a flask
  2. temperatureAfter cooling to room temperature
  3. filtrationthe precipitate is filtered
  4. washwashed with ethyl acetate
  5. additionExcess amount of water is added
  6. extractionextracted 4×
  7. dry with materialDried with sodium sulfate
  8. customevaporated
  9. customto give 2.7 g (59% yield) as a yellow solid

Sources & evidence

ORD record
ord-0249f25e3a274b8f844b699f74d11bf5
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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