Ammonia → HCID 10703303, compound

HRID 365492Notes

Reaction equation

HRID 365492 reaction equation
[NH2:1][CH:2]([CH2:5][C:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)[C:3]#[N:4].N>[Ni].CO>[CH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH2:15][C:6]=1[CH2:5][CH:2]([NH2:1])[CH2:3][NH2:4]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 10488190HCID 10488190, compound

Product 1

HCID 10703303HCID 10703303, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

A mixture composed of 2.57 g (13 mmol) of the nitrile obtained in Step 3, 120 ml of CH3OH, 2 g of Raney nickel and 50 ml of a solution of NH3 in CH3OH (7N) is hydrogenated under a pressure of one atmosphere for 16 hours. After filtration over Celite, the solution is concentrated and the residue is chromatographed on silica, eluting with a mixture of CH2Cl2 /CH3OH/NH4OH conc.=90/10/1, to yield the expected compound in the form of a colourless oil.

Workup

  1. filtrationAfter filtration over Celite
  2. concentrationthe solution is concentrated
  3. customthe residue is chromatographed on silica
  4. washeluting with a mixture of CH2Cl2 /CH3OH/NH4OH conc.=90/10/1

Sources & evidence

ORD record
ord-bec7969c647e4059b52f0764cfb460c9
Source dataset
uspto-grants-2000_10
Patent number
US06127396

Reaction notes

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