HCID 14801536, compound → HCID 14801568, compound

HRID 374380Notes

Reaction equation

HRID 374380 reaction equation
[CH:1]1([N:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH:42]3[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)[C:30]([NH:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-])=O)=[CH:35][CH:34]=3)=[O:31])[CH:23]=2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CN(C=O)C.[Pd].[C]>[NH2:39][C:36]1[CH:35]=[CH:34][C:33]([NH:32][C:30](=[O:31])[N:29]([CH2:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([CH2:21][N:8]([CH:1]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:9]([NH:11][C:12]3[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=3)=[O:10])[CH:23]=2)[CH:42]2[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]2)=[CH:38][CH:37]=1

Participants

4

Reactant 1

HCID 14801536HCID 14801536, compound

Product 1

HCID 14801568HCID 14801568, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3 g 1,3-bis[[1-cycloheptyl-3-(p-nitrophenyl)ureido]methyl]benzene (compound of Example 28) in 50 ml N,N'-dimethylformamide, was added 300 ml of 10% Pd-carbon powder, and the mixture was subjected to catalytic hydrogenation. After a predetermined volume of hydrogen gas was absorbed, the catalyst was filtered off, the solvent was distilled off under reduced pressure from the filtrate, and the residue was purified by silica gel column chromatography, giving 1.5 g of 1,3-bis[[3-(p-aminophenyl)-1-cycloheptylureido]methyl]benzene as amorphous powder. This was treated with ethanolic hydrogen chloride, and the solid thus obtained was recrystallized from aqueous ethanol, affording 1.1 g of 1,3-bis[[1-cycloheptyl-3-(p-aminophenyl)ureido]-methyl]benzene dihydrochloride.

Workup

  1. customAfter a predetermined volume of hydrogen gas was absorbed
  2. filtrationthe catalyst was filtered off
  3. distillationthe solvent was distilled off under reduced pressure from the filtrate
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-35aa9aa3517342f09312ff898cc57cb2
Source dataset
uspto-grants-1992_11
Patent number
US05166429

Reaction notes

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