Water → 1,4-Bis(4-(4-aminophenylmethyl)phenylmethyl)benzene

HRID 1377213Notes

Reaction equation

HRID 1377213 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][C:32]5[CH:37]=[CH:36][C:35]([N+:38]([O-])=O)=[CH:34][CH:33]=5)=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.O.[H][H]>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][C:32]5[CH:33]=[CH:34][C:35]([NH2:38])=[CH:36][CH:37]=5)=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 229198971,4-Bis(4-(4-nitrophenylmethyl)phenylmethyl)benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 223212851,4-Bis(4-(4-aminophenylmethyl)phenylmethyl)benzene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a 1-liter three-necked flask equipped with a stirring device and a nitrogen substituting device, 25.00 g of 1,4-bis(4-(4-nitrophenylmethyl)phenylmethyl)benzene was dissolved in 400 milliliters of tetrahydrofuran, 2.5 g of a Pd-C catalyst (a 5% product, containing 55.9% of water) was added and contacted with hydrogen gas while cooled with water at a normal pressure and then stirred. By recrystallizing the concentrate from a tetrahydrofuran solvent, 21.13 g of a diamino compound according to the invention, that is, 1,4-bis(4-(4-aminophenylmethyl)phenylmethyl)benzene was obtained. Melting point was from 177.9° to 179.7° C.

Workup

  1. customIn a 1-liter three-necked flask equipped with a stirring device
  2. additionwas added
  3. customBy recrystallizing the
  4. concentrationconcentrate from a tetrahydrofuran solvent, 21.13 g of a diamino compound

Sources & evidence

ORD record
ord-6fda7911689048748d31dc8ad3065654
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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