1,2-Dichloroethane → 2-Phenyl-2-(3-pyridyl)-4-chlorobutyronitrile

HRID 1415158Notes

Reaction equation

HRID 1415158 reaction equation
[C:1]1([CH:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC=CC=1.[CH2:22](Cl)[CH2:23][Cl:24]>>[C:1]1([C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)([CH2:22][CH2:23][Cl:24])[C:8]#[N:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 241BenzeneHCID 270956Phenyl(pyridin-3-yl)acetonitrile

Product 1

HCID 214836722-Phenyl-2-(3-pyridyl)-4-chlorobutyronitrile

Procedure

A solution of 19.3 parts of α-phenyl-3-pyridylacetonitrile in 140 parts by volume of dry benzene is treated with 4 parts of soda amide and the mixture is refluxed with stirring for 1 hour. The mixture is cooled to room temperature and ethylene dichloride 17.2 parts is added. The mixture is stirred and refluxed for 4 hours, cooled, washed with water and dried. Removal of solvent and isolation provides 2-phenyl-2-(3-pyridyl)-4-chlorobutyronitrile. Following the procedure set out in Example 9, 8.9 parts of 4-hydroxy-4-phenylpiperidine are reacted in 400 parts by volume of ethylene glycol monoethyl ether at reflux for 18 hours to provide 2-phenyl-2-(3-pyridyl)-4-(4-hydroxy-4-phenyl)piperidinobutyronitrile. Also following the procedures in Example 9 the latter compound is converted to 5-1-(phenyl)-1-(3-pyridyl)-3-[4-(4-hydroxy-4-phenyl)piperidino]propyl-1H-tetrazole and in turn to 5-1-(phenyl)-1-(3-pyridyl)-3-[4-(4-hydroxy-4-phenyl)piperidino]propyl-1,3,4-oxadiazole having the following structural formula ##STR46##

Workup

  1. temperaturethe mixture is refluxed
  2. stirringThe mixture is stirred
  3. temperaturerefluxed for 4 hours
  4. temperaturecooled
  5. washwashed with water
  6. customdried
  7. customRemoval of solvent and isolation

Sources & evidence

ORD record
ord-47cdd302e4cd43328ed5f8597f317d0b
Source dataset
uspto-grants-1977_01
Patent number
US04003904

Reaction notes

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