2-Chloronicotinonitrile → tert-Butyl4-(3-cyano-2-pyridinyl)-1-piperazinecarboxylate

HRID 645667Notes

Reaction equation

HRID 645667 reaction equation
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[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+]>CN(C)C=O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[CH:8][N:9]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 810792-ChloronicotinonitrileHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516893Potassium Bicarbonate

Product 1

HCID 22061422tert-Butyl4-(3-cyano-2-pyridinyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-Chloro-nicotinonitrile (2.04 g, 14.7 mmol) was added to a mixture of piperazine-1-carboxylic acid tert-butyl ester (2.74 g, 14.7 mmol) and potassium hydrogencarbonate (1.77 g, 17.6 mmol) in N,N-dimethylformamide (45 mL). The mixture was heated at 90° C. overnight. The solvent was removed and residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine then dried over magnesium sulfate and filtered. The solvent was removed to give the titled compound as an oil. 1H-NMR (400 MHz, DMSO-d6) δ 8.428 (dd, 1H); 8.08 (dd 1H); 6.95 (dd, 1H); 3.58 (m, 4H); 3.47 (m, 4H); 1.42 (s, 9H).

Workup

  1. customThe solvent was removed
  2. customresidue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-8b76c43a772a4f89aa7ba993427d3be0
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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