Water → HCID 18976656, compound

HRID 1377230Notes

Reaction equation

HRID 1377230 reaction equation
[N+:1]([C:4]1[CH:41]=[CH:40][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.O.[H][H]>[Pd].O1CCCC1>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([NH2:31])=[CH:29][CH:30]=4)=[CH:20][CH:19]=3)=[CH:13][CH:14]=2)=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 962WaterHCID 22920215HCID 22920215, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18976656HCID 18976656, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a 1-liter three-necked flask having a fit equipped with a stirring device and a nitrogen substituting device, 40.9 g of 1,3-bis(4-(4-nitrobenzyl)phenyl)-2-n-hexyl propane, 5 g of a Pd-C catalyst (a 5% product, containing 55.9% of water) and 300 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. Residues were dissolved in chloroform, and then subjected to a separating operation by a column chromatography with silica gel. By removing off the solvent again, 35.3 g of 1,3-bis(4-(4-aminobenzyl)phenyl)-2-n-hexyl propane was obtained as yellow oil.

Workup

  1. customIn a 1-liter three-necked flask having
  2. customa fit equipped with a stirring device
  3. additionwere introduced
  4. customAfter hydrogen absorption
  5. filtrationthe catalyst was filtered off
  6. concentrationthe solution was concentrated
  7. dissolutionResidues were dissolved in chloroform
  8. customBy removing off the solvent again

Sources & evidence

ORD record
ord-e1587350545f41ae8ea35eaeb7705e85
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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