Sodium Iodide → HCID 22321763, compound

HRID 496619Notes

Reaction equation

HRID 496619 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Na+].[I-].C([O-])([O-])=O.[K+].[K+].[C:22]([C:24]1[CH:29]=[C:28]([CH2:30][CH2:31]OS(C2C=CC=CC=2)(=O)=O)[CH:27]=[CH:26][N:25]=1)#[N:23].C(C1C=C(CCCl)C=CN=1)#N>CN(C=O)C.O.C(OCC)(=O)C>[C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:31][CH2:30][C:28]2[CH:27]=[CH:26][N:25]=[C:24]([C:22]#[N:23])[CH:29]=2)[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 22321675HCID 22321675, compoundHCID 22321715HCID 22321715, compound

Product 1

HCID 22321763HCID 22321763, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

1-Boc-piperazine (6.8 g, 36 mmol), NaI (2.7 g, 18 mmol), K2CO3 (3.0 g, 21.6 mmol) and a mixture of 2-cyano-4-[2-(benzenesulfonyloxy)ethyl]pyridine and 2-cyano-4-(2-chloroethyl)pyridine (2:1, 4.5 g, 18 mmol) was dissolved in DMF (50 mL) and heated to 80° C. overnight. The mixture was allowed to cool to room temperature and diluted with water and ethyl acetate. The layers were separated and the water layer extracted with ethyl acetate. The organic layers were combined, washed with water and brine, dried (Na2SO4), filtered and concentrated under vacuum to proved a dark oil (6.0 g). The crude product was purified by chromatography (SiO2, 1000:10:1-200:10:1 CH2Cl2:methanol:concentrated ammonium hydroxide) to provide 1-Boc-4-[2-(2-cyanopyridin-4-yl)ethyl]piperazine (4.0 g, 70%).

Workup

  1. temperatureto cool to room temperature
  2. customThe layers were separated
  3. extractionthe water layer extracted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by chromatography (SiO2, 1000:10:1-200:10:1 CH2Cl2:methanol:concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-9c58260209e348b28c4ba316f597b5dc
Source dataset
uspto-grants-2005_09
Patent number
US06946467B2

Reaction notes

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