N-Methyl-2-(4-nitrophenoxy)-N-[2-(4-nitrophenyl)ethyl]ethanamine → 1-(4-aminophenoxy)-2-[N-(4-aminophenethyl)-N-methylamino]ethane

HRID 1032664Notes

Reaction equation

HRID 1032664 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][CH2:10][N:11]([CH3:23])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C.[Ni]>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][CH2:10][N:11]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH3:23])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 14645090N-Methyl-2-(4-nitrophenoxy)-N-[2-(4-nitrophenyl)ethyl]ethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 146450981-(4-aminophenoxy)-2-[N-(4-aminophenethyl)-N-methylamino]ethaneYield 88.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(4-nitrophenoxy)-2-[N-methyl-N-(4-nitrophenethyl)amino]ethane (1.5 g) in ethanol (100 ml) was stirred for hours at room temperature under three atmospheres of hydrogen in the presence of Raney nickel ("Nicat 102"-Trade Mark). The reaction mixture was filtered and evaporated to dryness. The residual oil was re-dissolved in ether, filtered and evaporated to give a yellow solid (1.1 g), which was crystallised from ethyl acetate/60°-80° petroleum ether to give the title compound, (0.9 g), m.p. 73°-74°.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. dissolutionThe residual oil was re-dissolved in ether
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6cfc38dd03d747feb0732ad1a05274b8
Source dataset
uspto-grants-1990_09
Patent number
US04959366

Reaction notes

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