1,5-Dibromopentane → 1-(Pyridin-4-yl)cyclohexane-1-carbonitrile

HRID 966417Notes

Reaction equation

HRID 966417 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br>CN(C=O)C>[N:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 123966084-Pyridylacetonitrile hydrochloride

Product 1

HCID 223147891-(Pyridin-4-yl)cyclohexane-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3 g of 4-pyridylacetonitrile hydrochloride in 50 ml of DMF is cooled to 0° C., 2.6 g of 60% sodium hydride in oil are added portionwise and the mixture is left stirring at RT for 1 hour 30 minutes. The reaction mixture is cooled on an ice bath, 2.7 ml of 1,5-dibromopentane are added dropwise and this mixture is left stirring at RT for 48 hours. The reaction mixture is poured into saturated NH4CO solution and extracted with ether, the organic phase is washed three times with water and dried over MgSO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H gel, eluting with DCM and, then with a DCM/MeOH mixture (98/2; v/v). 2.5 g of the expected product are obtained; m.p.=79° C.

Workup

  1. waitthe mixture is left
  2. temperatureThe reaction mixture is cooled on an ice bath
  3. waitthis mixture is left
  4. stirringstirring at RT for 48 hours
  5. extractionextracted with ether
  6. washthe organic phase is washed three times with water
  7. dry with materialdried over MgSO4
  8. customthe solvent is evaporated off under vacuum
  9. customThe residue is chromatographed on silica H gel
  10. washeluting with DCM

Sources & evidence

ORD record
ord-e3e4075670234e469b4f20eac236540d
Source dataset
uspto-grants-2005_10
Patent number
US06951940B2

Reaction notes

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