Water → HCID 68726157, compound

HRID 2279655Notes

Reaction equation

HRID 2279655 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]#[N:9])[CH:2]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[H-].[Na+].O>C1COCC1.CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([C:8]#[N:9])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 809233-Pyridineacetonitrile

Product 1

HCID 68726157HCID 68726157, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of pyridin-3-yl-acetonitrile (14.65 g) and 1,5-dibromo-pentane (28.52 g) in THF (450 mL) and DMSO (450 mL) is added NaH (60% in mineral oil, 10.42 g) portionwise at 0° C. over 1 h. The mixture is allowed to warm to RT and stirred overnight. The reaction mixture is poured into water and extracted twice with EtOAc. The extract is concentrated and the residue is purified by silica gel chromatography to give 1-pyridin-3-yl-cyclohexanecarbonitrile.

Workup

  1. extractionextracted twice with EtOAc
  2. concentrationThe extract is concentrated
  3. customthe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-053a85e76225472dbacfd3c6c9284ffe
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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