Ammonia → HCID 58495619, compound

HRID 1190965Notes

Reaction equation

HRID 1190965 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][CH2:6][CH2:5][CH:4]([S:8][CH2:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:3]1.N>[Ni].C(O)C>[CH3:1][C:2]1([CH3:18])[CH2:7][CH2:6][CH2:5][CH:4]([S:8][CH2:9][C:10]2[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58495670HCID 58495670, compound

Product 1

HCID 58495619HCID 58495619, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

To a slurry of Raney Nickel (0.25 g, 50% in water) in ethanol (40 mL) add a solution of 4-[(3,3-dimethylcyclohexyl)thiomethyl]-benzonitrile (0.4 g, 1.54 mmol) in ethanol (5 mL) followed by aqueous ammonia (0.88 M, 2.5 mL) and hydrogenate the mixture in a Parr shaker at 60 psi for 3 h. Filter the mixture through Celite® washing the filter cake with ethanol. Remove the solvent in vacuo to obtain the title compound as an oil (0.4 g, 100%).

Workup

  1. customfor 3 h
  2. filtrationFilter the mixture through Celite®
  3. washwashing the filter cake with ethanol
  4. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-b8c26896cc5a41669b230b9a6a310978
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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