Ammonia → HCID 178495621, compound

HRID 1262483Notes

Reaction equation

HRID 1262483 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13](I)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[CH3:17][N:18](C)C=O.N>CCCCCCC>[CH3:1][O:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([C:17]#[N:18])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 178495623HCID 178495623, compound

Product 1

HCID 178495621HCID 178495621, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Into a 300 ml three-neck flask were added compound (E) (20.0 g, 0.061 mol), cuprous cyanide (6.3 g, 0.071 mol) and N,N-dimethylformamide (DMF) (63 ml). The mixture was agitated and refluxed for 6 hours while heating on a mantle heater. After completion of the reaction, the reaction mixture was cooled down to room temperature and a 28% aqueous ammonia (18 ml) was added, followed by agitating the mixture, adding n-heptane (50 ml) for extraction, filtering off an insoluble matter in the n-heptane layer, washing the layer with 6N-HCl (50 ml), further washing with water till the aqueous layer became neutral, concentrating under reduced pressure, recrystallizing the resulting raw crystals from ethanol (10 ml), filtering off and drying to obtain 4-(trans-4'-methyloxymethylcyclohexyl)benzonitrile (F) (6.4 g).

Workup

  1. temperaturerefluxed for 6 hours
  2. temperaturewhile heating on a mantle heater
  3. customAfter completion of the reaction
  4. stirringby agitating the mixture
  5. extractionfor extraction
  6. filtrationfiltering off an insoluble matter in the n-heptane layer
  7. washwashing the layer with 6N-HCl (50 ml)
  8. washfurther washing with water till the aqueous layer
  9. concentrationconcentrating under reduced pressure
  10. customrecrystallizing the resulting raw crystals from ethanol (10 ml)
  11. filtrationfiltering off
  12. customdrying

Sources & evidence

ORD record
ord-158073b5c93244c19791af49a8a9c6dd
Source dataset
uspto-grants-1984_06
Patent number
US04452719

Reaction notes

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