HCID 135428345, compound → 1,4-Bis(alpha-aminobenzyl)benzene

HRID 66186Notes

Reaction equation

HRID 66186 reaction equation
[C:1](=[N:23]O)([C:8]1[CH:13]=[CH:12][C:11]([C:14](=[N:21]O)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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]>[NH2:21][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([CH:1]([NH2:23])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 2

HCID 135428345HCID 135428345, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 203406881,4-Bis(alpha-aminobenzyl)benzene

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

The dioxime from Step 2 (30 g) is dissolved in ethyl alcohol (300 ml), saturated with ammonia gas and Raney nickel catalyst W-6 (2 g) added. The mixture is subjected to 700 psi hydrogen pressure and heated at 70° for 3 hours. The catalyst is removed by filtration and 220 ml of ethanol is removed by distillation. The pale yellow precipitate is filtered and dried. Yield 28 g (91% of theory) mp 123°-7°.

Workup

  1. addition(2 g) added
  2. temperatureheated at 70° for 3 hours
  3. customThe catalyst is removed by filtration and 220 ml of ethanol
  4. customis removed by distillation
  5. filtrationThe pale yellow precipitate is filtered
  6. customdried

Sources & evidence

ORD record
ord-23afa6dfa7bc4e65ba179f120e3c6d56
Source dataset
uspto-grants-1978_12
Patent number
US04130664

Reaction notes

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