N-Benzylideneaniline → N-Methylbenzylamine

HRID 55917

Reaction equation

HRID 55917 reaction equation
C(=CN)C1C=CC=CC=1.[CH:10](=[N:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Co]>[CH2:10]([NH:17][CH3:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:10]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 10858N-BenzylideneanilineHCID 155076Ethenamine, 2-phenyl-

Product 2

HCID 7669N-MethylbenzylamineHCID 66028Benzylaniline

Reagents, catalysts & solvents 1

HCID 104730CobaltCatalyst

Procedure

Imines were hydrogenated using in situ-generated complex 2. Hydrogenation of N-benzylidene benzylamine proceeded under 4 atm H2 at 60° C. to afford dibenzylamine in 84% isolated yield using 2 mol % of complex 2 (Table 2, entry 13). N-Benzylidenemethylamine and N-benzylideneaniline were also hydrogenated by the cobalt catalyst, affording N-benzyl methyl amine and N-benzylaniline in good yields (Table 2, entries 14 and 15). Previous examples of cobalt-catalyzed imine hydrogenation are scarce.

Workup

  1. customisolated
  2. customyield

Sources & evidence

ORD record
ord-4a4db7e6614b4d4ab660ea8ce57cdbad
Source dataset
uspto-grants-2016_09
Patent number
US09434666B2

Linked notes

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