4-(4-Chlorophenyl)-4-(4-iodophenyl)piperidine → 4-[4-(4-Chlorophenyl)piperidin-4-yl]benzonitrile

HRID 1798396Notes

Reaction equation

HRID 1798396 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cu][C:22]#[N:23]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([C:22]#[N:23])=[CH:16][CH:15]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 593319744-(4-Chlorophenyl)-4-(4-iodophenyl)piperidineHCID 178418546HCID 178418546, compound

Product 1

HCID 672357694-[4-(4-Chlorophenyl)piperidin-4-yl]benzonitrileYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-(4-chloro-phenyl)-4-(4-iodo-phenyl)-piperidine and copper (I) cyanide in DMF was heated at 140° C. under nitrogen for 6 hours then allowed to cool. The mixture was diluted with ethyl acetate, washed with a mixture of conc. ammonia and brine (×5), dried (MgSO4), filtered and concentrated to give a residue which was partially purified by column chromatography (SiO2), eluting with a gradient of 2M ammonia in methanol (5% to 10%) and dichloromethane to afford the title compound (46 mg, <16%). This was taken on to the next reaction without further purification. LCMS (PS-A2) Rt 2.39 min [M+H]+297.

Workup

  1. temperatureto cool
  2. washwashed with a mixture of conc. ammonia and brine (×5)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas partially purified by column chromatography (SiO2)
  8. washeluting with a gradient of 2M ammonia in methanol (5% to 10%) and dichloromethane

Sources & evidence

ORD record
ord-e5856cb9a72c45969ba4a101e47a599a
Source dataset
uspto-grants-2013_01
Patent number
US08343953B2

Reaction notes

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