HCID 86741304, compound → HCID 67897334, compound

HRID 1650207Notes

Reaction equation

HRID 1650207 reaction equation
[OH:1][CH:2]([C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=1)[CH2:3][NH:4][C:5]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:16]=1)=[CH:6][N+:7]([O-:9])=[O:8].[H][H]>C(O)C>[NH2:34][C:31]1[CH:30]=[CH:29][C:28]([CH:2]([OH:1])[CH2:3][NH:4][C:5]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:16]=2)=[CH:6][N+:7]([O-:9])=[O:8])=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 86741304HCID 86741304, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67897334HCID 67897334, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

With 15 ml of ethanol was mixed 0.8 g of N-[2-hydroxy-2-(4-nitrophenyl)ethyl]-2-nitro-N'-[3-(3-piperidinomethylphenoxy)propyl]-1,1-ethenediamine, and hydrogen gas was introduced thereinto in the presence of 0.1 g of 5% (by weight) palladium carbon at ordinary temperature and under atmospheric pressure for 7 hours until the absorption of hydrogen gas ceased. Subsequently, the catalyst was removed by filtration and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by a column chromotography (Wako Silica Gel C-200, eluent; chloroform:methanol=5:1 by volume) to obtain 0.3 g (yield 40%) of amorphous N-[2-(4-aminophenyl)-2-hydroxyethyl]-2-nitro-N'-[3-(3-piperidinomethylphenoxy)propyl]-1,1-ethenediamine.

Workup

  1. additionwas introduced
  2. customin the presence of 0.1 g of 5% (by weight) palladium carbon at ordinary temperature and under atmospheric pressure for 7 hours until the absorption of hydrogen gas
  3. customSubsequently, the catalyst was removed by filtration
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by a column chromotography (Wako Silica Gel C-200, eluent; chloroform:methanol=5:1 by volume)

Sources & evidence

ORD record
ord-5bcc263d39b54ed785cfc4489e20c45d
Source dataset
uspto-grants-1990_05
Patent number
US04923882

Reaction notes

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