4,4'-Dibenzoylbenzophenone trioxime → 1,1-Bis(alpha-amino-alpha-phenyl-p-tolyl)methylamine

HRID 442247Notes

Reaction equation

HRID 442247 reaction equation
[C:1](=[N:32]O)([C:8]1[CH:31]=[CH:30][C:11]([C:12](=[N:28]O)[C:13]2[CH:18]=[CH:17][C:16]([C:19](=[N:26]O)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.N.[Ni]>[NH2:26][CH:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:16]1[CH:15]=[CH:14][C:13]([CH:12]([NH2:28])[C:11]2[CH:30]=[CH:31][C:8]([CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[NH2:32])=[CH:9][CH:10]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 2

HCID 1364097304,4'-Dibenzoylbenzophenone trioximeHCID 178418361HCID 178418361, compound

Product 1

HCID 203407061,1-Bis(alpha-amino-alpha-phenyl-p-tolyl)methylamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

The trioxime from Step 2 (3 g) is dissolved in ethyl alcohol (250 ml) saturated with ammonia gas and Raney nickel W-6 (2 g) added. The mixture is subjected to 500 psi hydrogen pressure and heated to 90° for 2 hours. The catalyst is removed by filtration and 220 ml ethyl alcohol by distillation. A pale yellow crystalline material is filtered and dried. Yield 2.5 g (92% of theory) mp 182-185°. Calculated for C27H27 n3 : C, 82.4%; H, 6.92%; N, 10.68%. Found: C, 82.41%; H, 6.95%; N, 10.70%.

Workup

  1. addition(2 g) added
  2. temperatureheated to 90° for 2 hours
  3. customThe catalyst is removed by filtration and 220 ml ethyl alcohol by distillation
  4. filtrationA pale yellow crystalline material is filtered
  5. customdried

Sources & evidence

ORD record
ord-e869b7b46159414ab1826e25e22192c6
Source dataset
uspto-grants-1977_08
Patent number
US04044139

Reaction notes

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