Potassium Carbonate → 1,1-Dimethylethyl 4-(5-cyano-2-pyridinyl)-1-piperazinecarboxylate

HRID 2238675Notes

Reaction equation

HRID 2238675 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 27579561,1-Dimethylethyl 4-(5-cyano-2-pyridinyl)-1-piperazinecarboxylateYield 95.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 702 mg of 6-chloronicotinonitrile, 954 mg of t-butylpiperazin-1-carboxylate, 1.2 g of potassium carbonate, and 10 mL of N,N-dimethylacetamide, was stirred at room temperature for 3 hours, then heated to 60° C. and stirred further for 4 hours. After cooling the reaction mixture back to room temperature, water was added thereto, and was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and 1.39 g of t-butyl-4-(5-cyanopyridin-2-yl)piperazin-1-carboxylate [140-1] was obtained as a white solid.

Workup

  1. temperatureheated to 60° C.
  2. stirringstirred further for 4 hours
  3. temperatureAfter cooling the reaction mixture back to room temperature
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationthe insolubles were filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2969ff10f5e445c89fed5c2055d6f52b
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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