Water → HCID 22321292, compound

HRID 1377223Notes

Reaction equation

HRID 1377223 reaction equation
O.[N+:2]([C:5]1[CH:39]=[CH:38][C:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][CH:30]=4)=[CH:24][CH:23]=3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([O-])=O.[H][H]>[Pd].O1CCCC1>[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][C:29]4[CH:30]=[CH:31][C:32]([NH2:35])=[CH:33][CH:34]=4)=[CH:24][CH:23]=3)=[CH:14][CH:15]=2)=[CH:38][CH:39]=1

Participants

6

Reactant 3

HCID 962WaterHCID 22921193HCID 22921193, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22321292HCID 22321292, compoundYield 84.5%

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, 3.5 g of a Pd-C catalyst (a 5% product, containing 55.9% of water) and a solution of 35.0 g of 1,6-bis(4-(4-nitrobenzyl)phenyl)hexane in 200 milliliters of tetrahydrofuran were introduced, and contacted with hydrogen gas at a normal pressure with stirring. After hydrogen absorption was stopped, the catalyst was filtered off and the solution was concentrated. Crystals were dissolved in chloroform, subjected to a column chromatography treatment with active alumina and silica gel, and thereafter the solution was reconcentrated to give a concentrate, which was then recrystallized from a mixed solvent of toluene and denatured ethanol, to obtain 26.1 g of 1,6-bis(4-(4-aminobenzyl)phenyl)hexane. Melting point was from 111.4° to 112.2° C.

Workup

  1. customIn a 1-liter three-necked flask equipped with a stirring device
  2. additionwere introduced
  3. customAfter hydrogen absorption
  4. filtrationthe catalyst was filtered off
  5. concentrationthe solution was concentrated
  6. dissolutionCrystals were dissolved in chloroform
  7. customto give a concentrate, which
  8. customwas then recrystallized from a mixed solvent of toluene

Sources & evidence

ORD record
ord-90ac9bc79ed34d938c44f3e7c8c552cc
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

Loading…