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

HRID 478591Notes

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.[NH4+].[Cl-]>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

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 NH4Cl 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

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

Sources & evidence

ORD record: ord-57926b7131274264aae0597c49dafdcb
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642233B1

Reaction notes

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